For those managing multiple rental properties

Philadelphia, Pennsylvania
Buying & Selling Real Estate
3moFollow

For those managing multiple rental properties

Ajayi Bukola
Member since 2026 · 15 posts · 2 votes

For those managing multiple rental properties

What is one task that takes more time than it should?

Not necessarily the biggest challenge, just the thing that makes you think:

"There has to be a better way to do this."

Curious to hear what others are dealing with.

0Reply
223 views

8 Replies

Jump to latestLatest
  • Chris SeveneyBusiness Member
    Moderator
    Investor · VA · Member since 2015 · 21k+ posts · 19k+ votes
    3mo

    Bookkeeping - which is why it's typically best to outsource it 

    7e investments53 Reviews
    WebsiteView Page
    0Reply
    • Ajayi Bukola
      OP
      Member since 2026 · 15 posts · 2 votes
      3mo
      Quote from @Chris Seveney:

      Bookkeeping - which is why it's typically best to outsource it 




      @Chris Seveney

      Interesting that bookkeeping came up first. It seems like one of those tasks that feels manageable at the beginning but gets much harder once you start adding more properties. At what point do you think it makes sense for an investor to outsource it?


      0Reply
  • Peter MckernanBusiness Member
    Residential Real Estate Agent · Irvine, CA · Member since 2013 · 2k+ posts · 1k+ votes
    3mo

    Bookkeeping and also doing the repairs yourself. Many owners think they can just fix themselves to save $100-$200, but then end up realizing they cannot fix it right or cannot fix it at all. Get a less expensive handyman and get them on speed dial to get the stuff done you cannot do.

    The McKernan Group4.957 Reviews
    WebsiteView Page
    0Reply
    • Ajayi Bukola
      OP
      Member since 2026 · 15 posts · 2 votes
      3mo
      Quote from @Peter Mckernan:

      Bookkeeping and also doing the repairs yourself. Many owners think they can just fix themselves to save $100-$200, but then end up realizing they cannot fix it right or cannot fix it at all. Get a less expensive handyman and get them on speed dial to get the stuff done you cannot do.

      That's a great point. A lot of investors focus on the cost of hiring help but don't always factor in the value of their own time. Have you found that repairs or bookkeeping tend to become the bigger challenge as a portfolio grows?


      0Reply
    • Chris SeveneyBusiness Member
      Moderator
      Investor · VA · Member since 2015 · 21k+ posts · 19k+ votes
      3mo

      @Peter Mckernan early on my wife and I would spend weekends doing work and managing trades. That lasted about a year as it as sucking up too much time and time away from kids - that's actually how I got into note investing and do what I do now 

      7e investments53 Reviews
      WebsiteView Page
      0Reply
  • Andrea Fernandes
    Specialist · Goa, India · Member since 2026 · 175 posts · 36 votes
    3mo

    Bookkeeping and repairs coming up together makes sense — they're both death by a thousand small manual steps, not one big hard task.

    For bookkeeping specifically, a lot of the time sink isn't the accounting itself, it's the data entry getting there — chasing receipts, matching expenses to the right property, remembering to log something before it's forgotten. That part's usually automatable even before you bring in a bookkeeper: receipts get logged automatically the moment they happen instead of being reconstructed later.

    Repairs are similar — the actual fix takes however long it takes, but the coordination around it (getting the handyman scheduled, confirming it's done, tracking the cost against the right property) is where the hours quietly disappear.

    @Ajayi Bukola — to answer your outsourcing question: I'd say the trigger point isn't a specific portfolio size, it's when you notice you're spending more time tracking the work than actually reviewing the numbers. That's usually the signal it's time to either automate the logging or hand it off entirely.

    — Andrea

    0Reply
  • Matthew Tregoning
    Property Manager · Melbourne, FL · Member since 2019 · 353 posts · 150 votes
    3d

    The wasted trip is one coordination problem I’d try to remove first. Before a vendor heads over, confirm the access arrangements, the actual problem and any model number or photos they need. Then have one place to record the appointment and who confirmed it. Paying for a visit that ends with “I couldn’t get in” is frustrating for the resident, the owner and the person doing the work.

    0Reply
Join the conversationCreate a free account to reply, vote on answers and follow this thread.
Log InJoin for Free