We do have multiple goals for this property (personal use is very low on that list just due to work, crazy schedules, etc.) and they are panning out.

I had a brand new AC put in (May 2024), first guest after snapped the condensation pipe pulled the drain pan clear out.  

Hey Colby, it doesn't really matter that much when you do it but if you want to be more organized, you could just open up a LLC, get a TIN/EIN # and open up a bank account for it.

Repairs and maintenance will be significantly higher, because you are responsible for furnishings, appliances, HVAC, linens, pots, pans, etc.

New (young) tenant is renting an older SFH with a tin roof. 

This is only meant as a quick way you can filter potential deals and not waste your time on ones that have no chance to pan out. 

We'll see how this pans out.

Faster is not always a consequence of laziness.I'd say see what you can do with the current manager before you jump from the frying pan into the fire.

Depending on your current rent, I suspect you are likely to recoup your investment in saved rent pretty quickly which makes me think it’s going to end up as a great learning experience, even if the upside doesn’t pan out.Make sure you get clear divorce options for the partnership as living in a rundown trailer scrounging for money to fix it could end up rather stressful.

NY panned out, FL didn’t—and sort of just trusted fate.I’ve long been in love with Hudson Valley/Catskills—SO much is way overpriced right now, but there are pockets I feel strongly are up-and-coming/not overpriced just yet.