How to Self-Manage a Rental Property Portfolio: What We Learned Building Ours from Scratch
I did not set out to build a rental portfolio. I set out to survive.
That distinction matters, because I think a lot of people read blog posts about self managing rental properties and assume the author had a plan from the beginning. Some spreadsheet, some investor's playbook, some vision board. I had a teacher's paycheck, a mountain of divorce attorney bills, a spare bedroom, and a stubborn refusal to let any of it beat me.
What I have now is a portfolio of short term rental properties in Greensboro, NC, including three whole home rentals, two private bedrooms in the home Eric and I live in, a mid term tiny home ADU, and three traditional rentals. All of it within about a mile of Greensboro Country Club, near UNCG and Cone Health. All of it held in a trust we set up through an Elder Law attorney in Greensboro. And all of it built over roughly 25 years, one property at a time, starting from nothing.
This is the post I wish had existed when I started.
It Started in Flagstaff, Arizona
The first rental property I ever managed was a condo at Summit Park in Flagstaff, Arizona, in the late 1990s into the early 2000s. My then husband and I owned the unit, and I served on the HOA board of directors for that development, which turned out to be one of the most valuable pieces of accidental education I ever received.
I learned about fire suppression systems and how they work in uninsulated spaces. I learned how HOA governance actually functions from the inside: the budgets, the assessments, the neighbor dynamics, the fine line between enforcing community standards and being a busybody. I learned that the people who show up to serve on HOA boards are not always the people you would most want making decisions, and that showing up anyway matters. I have written more about that experience in my post on running a self managed HOA.
And I learned what it felt like to be a landlord: to hand over a set of keys to someone and trust them with something you own, something you are responsible for, something that is simultaneously an asset, a liability, and someone's home.
That is the tension that never goes away. The sooner you make peace with it, the better.
Then Came Wafco Mills
When I eventually landed in Greensboro, I bought a unit at Wafco Mills, a community of 66 condominiums built in the 1980s in the College Hill neighborhood, with the specific intention of renting it out if I ever found the right partner to build something with.
I want to be clear about what Wafco Mills is, because people confuse it with Historic Wafco Mills constantly, and they are two entirely separate developments that happen to share the same city block. Historic Wafco Mills is the original 1893 mill building, converted to 28 residential condominiums, managed by its own HOA. Wafco Mills is the 66 unit condominium development built in the 1980s on the same property, managed by a completely separate HOA. My unit is at Wafco Mills, not Historic Wafco Mills. Different buildings, different governance, different ownership structure entirely. You can learn more about the distinction at wafcomills.com.
I also rented out the second bedroom of my Wafco Mills unit while I was living there, partly to offset a wall of divorce attorney bills and partly because a teacher's paycheck in North Carolina does not leave much margin.
Renting a room in your own home is one of the most clarifying experiences in landlording. There is nowhere to hide. You are the property manager, the maintenance crew, the lease enforcer, and the neighbor, all at once. You find out fast whether you have the temperament for this.
Turns out, I do. And in 2018, just before we purchased our first joint investment property together, I got my North Carolina real estate license. That first transaction under my new license was 907 W. Wendover Ave. It felt right that way.
Building the Portfolio, One Rehab at a Time
Here is the sequence, because people always ask.
| Property | Current Use | Type |
|---|---|---|
| 907 W. Wendover Ave | Idlewood House | Traditional rental |
| 909 W. Wendover Ave | Your Mom's Place (Joy and Eric's primary residence, two private rooms upstairs on Airbnb) | Short term rental private rooms |
| 905 W. Wendover Ave | Hunsucker's Place | Whole home short term rental |
| 905 W. Wendover Ave (ADU) | Urban Birdhouse Tiny Home ADU | Mid term furnished rental |
| 903 W. Wendover Ave | Library of Ivy and Ellie | Whole home short term rental |
| 1007 Grayland St | My Sister's House | Whole home short term rental |
| 622 B Walker Ave (Wafco Mills) | Downtown Greensboro College Hill Condo | Traditional rental |
| King Edward House | King Edward House | Traditional rental |
Every one of those properties is now held in a trust we established through an Elder Law attorney here in Greensboro. If you are building a portfolio and have not thought about asset protection and estate planning, that conversation is worth having sooner rather than later.
A few things that are true across all the rehabs:
Every house lies to you during inspection.
You think you know what you are getting into. You do not know what you are getting into. At 1007 Grayland, we discovered the entire roof was rotten. The basement was flooding, not from weather but from a broken water line between the street and the house that had been leaking so long the previous family could not afford to pay the water bill or fix it. The floor was visibly sagging under the kitchen and bath. The back addition and deck were so far gone they had to come off entirely.
We rented four dumpsters. We posted salvageable items on Facebook Marketplace. People showed up at all hours to dig through vintage t shirts and mementos pulled from a flooded attic. I sorted through the contents of that house for days, and it was powerfully sad. Sixty years of a family's life. That weight does not leave you.
Sustainability is not a buzzword. It is a budget decision.
At Grayland, I sourced cabinets from Architectural Salvage in Greensboro, all wood, $25 each, and had our carpenter build new ones to match. I found a vintage clawfoot tub for $350 that would cost less and go to landfill never instead of immediately. These choices keep costs lower and keep good materials out of dumpsters. They also give the finished spaces a character that a flat pack renovation simply cannot replicate. Guests notice. Long term tenants notice. It matters. You can read more about how we approach this in our post on the sustainability and rehab of 1007 Grayland.
Neighbors are not a side effect of property ownership. They are part of the investment.
Every home I have ever owned or managed has had neighbors, and the relationship with those neighbors has always mattered. My mother taught me this by bringing zucchini bread across the street when a neighbor's TV was too loud at 2 a.m. You handle it in person, you handle it with food, you handle it with kindness, and usually that is the end of it. The same principle applies when you own rental properties in a residential neighborhood. Go introduce yourself. Know the people on either side. Be reachable. Be reasonable. I have written about the role neighbors have played throughout my life in my post simply titled Neighbors.
Why We Do Not Use a Property Management Company
People ask us this constantly. The answer is simple: we care about the people who live in and visit our homes, and a management company cannot care about that the way we do.
When a guest or tenant reaches out to us, they are talking to Joy or Eric. Not a call center. Not a ticketing system. Not someone who manages 200 other units and will get back to you in three to five business days. According to DoorLoop's 2024 Property Management Industry Report, about 35% of property management firms manage between 101 and 500 units, and many individual managers are responsible for 50 to 100 doors on their own. That is not a relationship. That is triage.
We manage a small number of homes intentionally. We know every property, every guest, every vendor. When our cleaning team flags something that needs attention, we fix it. When a guest leaves feedback, we respond and we actually adjust. We have written about this philosophy in detail in our post What Kind of Landlords We Are: Why We Keep It Local, Real, and Respectful. It comes down to respect going both ways, and showing up as real people rather than a faceless entity.
That said, self managing is not for everyone. Here is what it actually requires.
What Self Managing Actually Looks Like
You are always on call, but you set the terms.
Guests and tenants will contact you outside of business hours. You need a system for after hours maintenance emergencies versus non emergencies, and you need to communicate that system clearly upfront. A leaking pipe at midnight is an emergency. A squeaky cabinet hinge is not. Define it in writing before anyone moves in.
Good vendors are your infrastructure.
We work with a trusted network of local vendors, cleaners, plumbers, carpenters, HVAC techs, who know our properties and who we pay fairly and promptly. That relationship is worth protecting. When a vendor stops meeting our standards, we make a change, because doing what is right matters more than doing what is easy. When you find people who are excellent and reliable, you hold onto them.
Your lease and your house rules are your first line of protection.
For short term rentals, your listing's house rules and guest screening do the work that a lease does for long term rentals. Be clear, be specific, and do not bury the important stuff in paragraph fourteen. For long term tenants, use a lease that is compliant with NC landlord tenant law under Chapter 42, address everything in writing, and document the condition of the property at move in with photos and a signed checklist.
Track everything financially from day one.
Even when you are starting with one property, build the habit. Separate bank accounts for rental income. Keep every receipt. Know your numbers, not just rent collected but maintenance costs, insurance, vacancy rate, and what you are actually netting after all of it. We use RentRedi for our traditional rental management, which handles rent collection, maintenance tracking, and tenant communication in one place. For our short term rentals, we manage dynamic pricing through PriceLabs, which replaced Airbnb's Smart Pricing across all four of our listings.
Respect is non negotiable in both directions.
We love hosting respectful guests and responsible tenants. We also reserve the right not to renew a lease or decline a future stay when communication becomes hostile or adversarial. We are real people, not a corporation with an in house legal department. We make mistakes, and when we do, we own them and make it right. What we will not do is operate under the constant threat of being treated as an adversary.
HOA and regulatory compliance is real work.
If your rental is within an HOA, you need to understand the rules and stay ahead of them. The governance of a self managed HOA is complex, and as a housing provider operating within one, your tenants and guests become your proxy in that community whether you intend it or not. Know what the CC&Rs require. Know what the city requires. Know what the state requires. Regulations affecting small housing providers are an ongoing conversation worth paying attention to, and advocacy matters.
Put your properties in a trust.
This one took us a few years to get around to and I wish we had done it sooner. Working with an Elder Law attorney to hold your properties in a trust protects your assets, simplifies estate planning, and gives you a legal structure that grows with your portfolio. If you need a referral to an Elder Law attorney in Greensboro, reach out and I am happy to point you in the right direction.
Think holistically about the health of your home and your guests.
One thing I have become more intentional about over the years is what goes into and onto our properties in terms of products, materials, and practices. My daughter Ivy is a certified herbalist who writes extensively about the intersection of health and home. Her article on essential oil risks and endocrine disruption changed how I think about what we use to clean and scent our rentals. If you have pet friendly properties like ours, her guides on holistic pet care and natural flea and tick prevention are genuinely useful resources to share with guests.
The Part Nobody Talks About
Building a rental portfolio is slow. It is patient work. It is showing up at a flooded basement at 7 a.m. and making decisions under pressure with incomplete information. It is realizing mid rehab that the entire back wall has to come off. It is four dumpsters when you thought it would be one.
It is also deeply satisfying in a way that is hard to explain to someone who has not done it. There is something about taking a house that has been neglected or damaged or just plain used up and returning it to something livable, beautiful even, that feels like meaningful work. We have done that across every one of these properties now, each one different, each one teaching us something we did not know before.
We started because I needed to survive. We kept going because we found out we were good at it, and because we genuinely love what these homes make possible, for guests, for tenants, for the neighborhoods they are in, and for us.
If you are thinking about self managing a rental property and you have questions, reach out. This is exactly the kind of thing I like to talk about.
Joy Watson, Realtor® | Joy Watson Real Estate
Serving Greensboro, NC & the Piedmont Triad
(928) 699-8883 | joy@joywatsonrealestate.com
joywatsonrealestate.com
License #307423 | Firm License #C37131
Equal Housing Opportunity 🏠