That said, using a light structure makes automation and reminders much easier without adding complexity.What works well for self-managing landlords is something like:[Property] – [Task] – [Urgency/Type]Examples:“Oak St Duplex – HVAC Check – Annual”“Maple Ave – Lease Renewal – Unit 2”This lets you quickly filter/search and also trigger automations later if you want to, but it’s not mandatory.On maintenance + emergency callsWhat you’re describing is exactly where most tools fall apart for small landlords — they’re built for volume and vendor density that just doesn’t exist in smaller cities like Pittsburgh.

Infrastructure, utilities, roads, pads, and structures all have different classifications, and if someone starts allocating numbers without a defensible basis, that’s where problems show up.For my phased build, I’m trying to keep everything clean and tied to actual engineering, construction costs, and third‑party documentation so there’s no guesswork later.

I’ve seen rookies get in trouble when they chase BRRR for long-term wealth but run it like a flip without the right capital structure or exit flexibility.

These run for weeks, causing mold and structural rot that insurance often denies as "gradual damage."2.

If a current short term rental DSCR refinance, they will look at the short term rental history and structure the loan around that.

• Any structures you didn’t initially consider but ended up working well?

If you are an attorney experienced with Florida land trusts and multistate LLC structures and are able to assist, please DM me.

If rent can’t comfortably cover mortgage, HOA, taxes, insurance, and some repair cushion, you’re subsidizing the property while also taking on the risk of future fee increases or assessments.Also look at the HOA’s financial health — reserves, upcoming projects, and assessment history matter more than online value estimates right now.If the numbers don’t make sense and fees keep trending up, that’s a structural issue, not just a temporary market dip.

Explain how you do things - leases, marketing for leases, general operations & structure - how y’all do inspections & if included in your fees, what you will provide on an ongoing basis (platform reports, placeholder for tenants to call & submit maintenance requests, take payments, handle communications, late payments, occasional drive by’s to check on place, handle evictions, move ins & outs, turnovers & make ready’s).

The big risk items are setbacks zoning coverage and any structural work or foundation work that was done without engineering.