From the surface it looks decent...however I would get an insurance quote and see if you can squeeze any information about delinquency rates in the HOA.

If you install during the hotter season you risk the floor most likely gapping and coming apart during the winter or buckling during the inverse.If you are set on some type of hard surface flooring a dehumidifier could help reduce some of the risk for the time being, since changes in humidity and moisture are actually what cause expansion and contraction not temperature, they usually are just tied hand in hand.The larger the room the more the floor will move.

On the surface you might assume that the all-in cap rate is always lower that the going-in cap rate, and in many cases it is, but it doesn't have to be.

At a certain point, I started noticing certain "road markings" - spray-painted designations that would appear on the streets, or on paved-surfaces in the immediate area.

If a valid will surfaces, the decision might be made easier.

For what it's worth, moving forward, you can sell off using a Limited Warranty Deed (like REO banks typically do) which limits your exposure back to the date when you actually received title, but not further.And as also noted, you can definitely use the same title company to re-insure if a problem does surface as effectively they are already 'on the hook' for that issue.

It's 1200sq ft (probably more because it certainly didn't feel like 1200 sq ft when we looked around) sold as-is with special warranty deed and on the surface there are very little cosmectic problems with the house except for the carpet and walls and one moisture damaged window.

lets go with the big money ticket items like roof inspections to include gutter systems that run into sewers as well as any drainage issues.

I assume some of this cost will go to the exterior for aesthetic improvements (paint, landscaping, signage, etc) and some will go to deferred maintenance (new roof, new boiler, repairs to mechanicals, electrical or plumbing systems, site drainage, sewers, etc).

Hearing your story reminds me of the one from 2015, where I spent an extra $2,000 on drainage due to the 2' of water in the basement when I bought the house.