It's not something we taught them or fostered as their property manager. 

How are you staying on top of building compliance across DOB, HPD, FDNY, DEP, LL97, LL152, annual tenant notices, registrations, inspections, and everything else?

I’ve had a couple moments where something caught me...

Quote from @Patricia Keely: As portfolios grow, a lot of investors hit a point where what “worked fine” at 1–2 properties starts to feel very different at 5, 10, or 20+ doors.For those currently using a property management company (or considering one), I’m curious to hear your experiences as you’ve scaled:What’s working well with your PM?

I’ve structured Florida deals this way and the big thing to understand is that Florida land trusts are privacy tools, not a shield from Florida compliance.A few practical points from experience:• The beneficial owner LLC does not need to be Florida-registered by default, but the moment it’s actively operating (collecting rent, signing leases, managing vendors), Florida can argue it’s doing business in-state.• Using an out-of-state LLC as trustee is common, but banks, insurers, and some counties will still require Florida qualification somewhere in the stack.• If you plan to self-manage or control leasing decisions, a Florida-registered management entity (even a simple LLC) often keeps things cleaner and reduces audit risk.• Most investors underestimate how quickly sales tax, DBPR, and local licensing issues come into play, especially with short-term or mixed-use rentals.Land trusts work well for title holding + privacy, but they don’t replace proper entity registration or compliance.

Loan terms often affect reserve planning, renovation schedules, and maintenance decisions.Property managers and owners — how much does financing influence your operational planning?

Co-own a 25 year old property management company that focuses primarily on Red River Gorge.

Will likely self-manage in the future from seeing property management done and having more time.Thank you!

I am with those that manage through the built in tools.

My wife also has a property management company for single family home and HOA property management.

ESPM was not the best property management firm I've ever worked with.