Biggest struggles self managing??

Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes

Self managing in itself is stressful, let's be honest. What do you find to be your biggest struggle with the day to day management of your property? (commercial, long term, vacation)

1 Reply

3,644 views

Most Popular Reply

James JonesPro Member

Investor · Collierville, TN 38017 · Member since 2017 · 968 posts · 664 votes

At 236 properties, the struggle is not any one call. It is volume.

One dripping faucet is nothing. Thirty small things in a week will bury you if every one lands on your phone the same way.

What works for me in Memphis is triage by habitability and money. Water running, heat out, sewer backed up, no power — that is same-day. Everything else gets batched, not chased one by one. Requests come in writing, with a photo. That cuts the 2 a.m. noise and gives you a record.

And track repeat addresses. A house that calls every month is usually not a tenant problem. It is a rehab problem I missed. Fix the root once, or you pay for it twelve times. Self-managing at scale is a system, not a personality.

2 Reply

See this reply in the discussion

26 Replies

Jump to latestLatest

Sort by

Randy Schell
Member since 2026 · 255 posts · 37 votes
5d
Malory, the late night texts about a dripping faucet get me every time, and nobody warns you about that part. One thing that calms it down for a lot of owners is telling tenants up front which hours you answer the small stuff, so only true emergencies ring at 2 AM....
Randy, Bunklow
1 Reply
- Diana KhanPro Member
  Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 701 posts · 251 votes
  5d
  Quote from @Randy Schell:
  Malory, the late night texts about a dripping faucet get me every time, and nobody warns you about that part. One thing that calms it down for a lot of owners is telling tenants up front which hours you answer the small stuff, so only true emergencies ring at 2 AM....
  Randy, Bunklow
  @Malory Medaglia, I'd say one of the biggest challenges with self managing is keeping up with tenant issues while making sure everything is properly documented. It's easy to get caught up in repairs, rent payments, and everyday concerns, but keeping good records is just as important.
  I'm a real estate attorney and investor based in Maryland, and I work with landlords on leases, tenant disputes, and other property matters. I've seen how small issues can become bigger problems when there's no clear record of what happened or how something was handled.
  I appreciate you bringing this up, @Malory Medaglia. Managing rental properties takes a lot more work than people sometimes realize. Happy to stay connected!
  [email protected]240-266-0291
  1 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  4d
  It's almost like the 2 AM faucet text is a rite of passage! Totally agree. Setting those expectations at move-in makes a HUGE difference.
  0 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @Diana Khan Thanks Diana! Documentation is one of those things that feels optional until you need it… We try to log every request with the date, photos, and how it was resolved, and it’s made a big difference when questions come up later. Appreciate you jumping in!
  1 Reply
- Joseph Thon
  Real Estate Broker · Rochester, NY · Member since 2026 · 13 posts · 1 vote
  13h
  That's something I was getting overwhelmed with as I scaled my portfolio. Trying to find texts, emails, and phone call logs drove me insane.
  I refuse to give out my cell phone anymore. If a tenant texts me, I don't directly respond. I respond on my property management platform so that the communication is logged and documented.
  The hardest part is holding myself accountable to that system. Because it's wayyyy easier to simply respond to their text. You have to be disciplined and stick to the system and that's hard for people to do consistently
  0 Reply
Lorelai Germain
Real Estate Consultant · Seattle, WA · Member since 2026 · 18 posts · 4 votes
5d
I think one challenge that gets overlooked is noticing patterns before they become expensive problems. For example, if maintenance costs keep increasing or the same repairs come up repeatedly, it might be worth investigating what's driving them. When you're busy handling everything yourself, those trends can easily go unnoticed until they start affecting your bottom line.
2 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  4d
  Love this! It’s so easy to treat each repair as a one-off when you’re in the weeds. Looking back at maintenance history every so often also can tell you a lot about where the real problem is. This is something I see too often!
  0 Reply
Jaron WallingPro Member
Rental Property Investor · Indianapolis, IN · Member since 2018 · 4k+ posts · 4k+ votes
5d
Our big issue is tenants not communicating issues; unreported issues and tenants doing DIY repairs in our rentals. Sounds great right? It's not benefit. Properties can go downhill due to negligence, lack of communication, or not enough inspections. Poorly fixed issues by the tenant can be a band-aid and I don't accept band-aids to fix legitimate issues.
Example; I ask our tenants if anything looks out of place or broken almost yearly. Tenant says "everything is fine, no issues." One of our properties had stairs that were in rough shape, but when I did an inspection I found both handrails completely broken and the concrete in worse shape than I remember. I see a red flag and safety issue; tenant see's a rent increase and doesn't complain. I've come to the conclusion this dynamic never ends. It's just part of rentals and PM.
We spent $1800 and rebuilt the stairs. If don't reinvest into what you have there's no point in buying more.
1 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @Jaron Walling “Everything’s fine” is the answer we hear most often too.. During our inspections we are constantly having our eye out for items that might not seem like a big deal to the tenant, but down the line can be costly. Tenants don’t always notice wear, or they don’t want to bring it up. I absolutely agree, this is just a part of PM!
  0 Reply
- Jaron WallingPro Member
  Rental Property Investor · Indianapolis, IN · Member since 2018 · 4k+ posts · 4k+ votes
  17h
  It's just the prospective of renting vs. owning and I get it. I rented four different houses during college (almost every side of of campus) and did the same thing. Only one landlord during that time actually did inspections on the house. The one that did was the best landlord we ever had. She even mowed our yard.
  
  I guess we didn't get the cops called enough.
  0 Reply
James JonesPro Member
Investor · Collierville, TN 38017 · Member since 2017 · 968 posts · 664 votes
4d
At 236 properties, the struggle is not any one call. It is volume.
One dripping faucet is nothing. Thirty small things in a week will bury you if every one lands on your phone the same way.
What works for me in Memphis is triage by habitability and money. Water running, heat out, sewer backed up, no power — that is same-day. Everything else gets batched, not chased one by one. Requests come in writing, with a photo. That cuts the 2 a.m. noise and gives you a record.
And track repeat addresses. A house that calls every month is usually not a tenant problem. It is a rehab problem I missed. Fix the root once, or you pay for it twelve times. Self-managing at scale is a system, not a personality.
2 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @James Jones This really hits home. We manage 350+ units, and you’re right, it’s never one call that gets you, it’s the volume!! Triage is what keeps it manageable for us too. Anything involving water, heat, power, or sewer gets handled same day, and everything else gets scheduled and grouped so our maintenance team isn’t running across town for one small fix at a time. Your point about repeat addresses is a good one. When the same unit keeps coming up, it’s usually worth stepping back and fixing the root cause instead of patching it again. Great insight!
  0 Reply
Matthew MorrowBusiness Member
Investor · PA - NY - NJ · Member since 2019 · 927 posts · 331 votes
4d
@Malory Medaglia for me it's keeping everything documented while still treating tenants like people. Most tenants are great, and it's easy to get relaxed about the paperwork. Then a payment gets missed or a platform delays a rent payment and you wish everything had been written down. Being nice and enforcing the lease aren't opposites, but it took me a while to get comfortable with that. Keep us posted on what you hear.
[email protected]484-791-6200
CORE Team | Realty ONE Group Supreme548 Reviews
Website View Page
0 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @Matthew Morrow This is such a good point, and it’s something a lot of owners struggle with. When you have a great tenant, it feels a little awkward to keep everything formal, but that’s usually when it matters most. A delayed payment or a quick verbal agreement about a repair can turn into a real issue if there’s nothing in writing to look back on. We try to keep every conversation about rent, repairs, and lease changes in writing, even when the relationship is great. It isn’t about distrust. It just keeps everyone on the same page. Tenants usually appreciate knowing exactly what to expect and where things stand. Thanks for sharing!
  0 Reply
Lee Futcher
Technology · Vancouver, BC · Member since 2026 · 90 posts · 12 votes
1d
Hi Malory,
I love that you asked this, because the answers here are a goldmine. James's point about repeat addresses really stuck with me, and you picked up on it too: when you're in the weeds, every repair feels like a one-off, so nobody sees the pattern until it's expensive.
For me the biggest struggle is that the information is scattered. One request is a text, the next is a voicemail, the photo is in someone's camera roll and the invoice is in an email. The history that would show you the pattern technically exists, but nobody can see it all in one place.
That's where I've seen AI do something genuinely useful for small landlords. Every request, whatever channel it arrives on, gets logged against the unit with the photo, the date and what was done. Once a month it reads back through that history and flags things like "third water issue at this address since spring" or "this vendor's repairs keep coming back." It covers the documentation side Diana and Matthew mentioned too, because the record builds itself as you go.
Since you run leasing and management in Beaufort, I'm curious: do your owners ever ask to see the maintenance history before they approve a bigger repair?
Cheers,
Lee
1 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @Lee Futcher Thanks Lee! Scattered information is a real challenge for self managers. Your point to use AI is wonderful. It makes sure everything lands in one spot and you are able to keep record of the conversations easily. To answer your question, our investors have access to an Investor Portal where they can see every maintenance request and repair at their unit. Some owners do ask for a simpler breakdown of those issues from time to time, which we’re always happy to put together. When our team notices our maintenance company or vendors going out to the same unit for the same issue more than once, we put together a game plan to tackle the root of the problem head on. That way the calls stop and the expenses don’t keep piling up. Great question!
  1 Reply
Harrison C.
Member since 2017 · 79 posts · 35 votes
1d
Malory, for us it was money that touches more than one person. We rent houses by the room, so one water or power bill gets split between five people who moved in on different days.
The first few months that bill caused more texts than every repair put together. What fixed it was boring: split by days lived in the house that month, send everyone the bill photo and the math the same day it comes in, and have it due on the same day as rent so nobody gets a surprise in the middle of the month.
Second place was move-out. Photos at move-in, room by room, dated, saved where you can find them in a year. Without them every deposit talk turns into your word against theirs.
James is right that the rest is volume. Requests in writing with a photo, batched unless water, heat, power or sewer.
1 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  22h
  @Harrison C. Thanks for sharing this, Harrison! Prorating by days lived in the home is a smart and fair way to handle it, and tying it to the rent due date makes a lot of sense. We don’t manage room rentals ourselves, but we see them all the time in our area since we have a lot of military and hospital staff coming through on shorter assignments. I’m curious how your overall experience has been with renting by the room. Has it been worth the extra work compared to leasing the whole house? I’m also wondering if you’ve ever thought about covering the utilities yourself and building that cost into a higher rental rate instead of splitting the bills. It seems like it could cut down on a lot of those texts, but I’d love to hear your take on whether that’s worked or not!
  0 Reply
Harrison C.
Member since 2017 · 79 posts · 35 votes
21h
Malory, for us it's been worth it, but go in knowing the trade. A house brings in more rented room by room than rented whole, and one empty room in a five-bedroom house is a fifth of the rent, not all of it. The cost is more people and more small stuff: the shared kitchen and bathrooms need a cleaner on a schedule, and rooms change hands more often than a whole house does.
On utilities, we do a bit of both. Rent covers the first $100 of utilities each month, and only what's above that gets split by days lived. That keeps the small months quiet, and if someone runs a space heater all winter, the house isn't eating the whole bill.
All-inclusive works too, it's just a guess you have to make before you see the bills. If you go that way, price it off your most expensive winter month, not the yearly average, and put a fair-use line in the lease so one person can't run it up on everyone else.
2 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  20h
  @Harrison C. This is so helpful, thank you for coming back with the details! Covering the first $100 and splitting only the overage is a really clever middle ground. It keeps the small months quiet but still protects you when someone cranks the heat all winter. Pricing off the most expensive winter month instead of the yearly average is great advice too, because that’s exactly where an all-inclusive rate can quietly eat into your margins. I’ll definitely be passing this along to a few owners in our area who’ve been considering rooms for traveling nurses. Great insight!
  0 Reply
James Pelton
Technology · Member since 2026 · 3 posts · 1 vote
21h
@Malory Medaglia, from working on this with my business partner, the part that comes up most is that every request arrives through a different channel. The tenant texts, the plumber calls, the co-owner emails, and by Friday nobody can say which unit still has something open.
What helps is one running list per property, with a status on every item (open, scheduled, done). Ask the tenant for one photo when they report it. Then take five minutes on Friday to chase anything that's been open more than a week.
It also makes the 2 AM texts easier to sort, because you can see what's already scheduled.
1 Reply
- Malory Medaglia
  OP
  Property Manager · Beaufort, SC · Member since 2024 · 17 posts · 4 votes
  20h
  @James Pelton Totally agree, the multiple-channels problem is real! A tenant texts, a vendor calls, an owner emails, and suddenly nobody’s sure what’s still open. A simple status on every item makes such a difference, and asking for one photo upfront saves a lot of back and forth. That Friday check on anything open more than a week is a great habit, too. It’s an easy way to catch things before a tenant has to follow up. Thanks for sharing!
  0 Reply
- Matthew MorrowBusiness Member
  Investor · PA - NY - NJ · Member since 2019 · 927 posts · 331 votes
  47m
  Quote from @Malory Medaglia:
  @James Pelton Totally agree, the multiple-channels problem is real! A tenant texts, a vendor calls, an owner emails, and suddenly nobody’s sure what’s still open. A simple status on every item makes such a difference, and asking for one photo upfront saves a lot of back and forth. That Friday check on anything open more than a week is a great habit, too. It’s an easy way to catch things before a tenant has to follow up. Thanks for sharing!
  Exactly. The good tenants are the ones you get relaxed with, and that's when a handshake deal turns into a misunderstanding. Writing it down protects the relationship as much as the property.
  [email protected]484-791-6200
  CORE Team | Realty ONE Group Supreme548 Reviews
  Website View Page
  0 Reply
Mona L.
New to Real Estate · Apopka, FL · Member since 2025 · 16 posts · 23 votes
18h
Honestly, from my experience as a PM, one of the biggest struggles I see with owners who self-manage is lack of consistency. If you set a rule or policy, stick to it. And if you tell a tenant you're going to do something, follow through.
That's where accountability starts. If tenants see that rules change depending on the situation, or that things you said you'd handle don't get followed up on, it becomes much harder to hold them accountable on their end. Be consistent, document everything, and don't make promises you can't follow through on.
0 Reply
Daniel Jung
Member since 2026 · 67 posts · 23 votes
18h
For me the hardest part is being the whole operation in one person. You are the leasing agent, the bookkeeper, the dispatcher and the person a tenant calls when you are already in the middle of something else, so there is no natural off switch. What made it manageable was writing things down as if someone else might have to step in tomorrow. One list of trusted vendors, one place for lease dates and inspections, simple templates for the messages you send over and over, and a backup person who can at least take a call in an emergency. None of that removes the work, but it stops every problem living only in your head, which is where most of the stress actually comes from.
1 Reply
Lee Futcher
Technology · Vancouver, BC · Member since 2026 · 90 posts · 12 votes
2h
Hey Malory,
Thanks for coming back to this, and I really like the investor portal approach. Giving owners a place to see every request and repair on their own unit answers most questions before they get asked.
The part that stood out to me was your team spotting the same issue at the same unit and building a plan to fix the root of it. That's where the real savings are, because the cost isn't one repair, it's the same repair three or four times a year.
One idea that pairs well with what you're already doing: when you put together that simpler breakdown for an owner, lead with anything that's repeated. Owners tend to trust a manager a lot more when the manager points out the pattern before they do.
Appreciate you sharing how your team handles it,
Lee
0 Reply

Join the conversationCreate a free account to reply, vote on answers and follow this thread.