This is fairly obvious as to why.

Be careful, the ADA only recognizes dogs for service animals, but residential rentals fall under Fair Housing that accepts any animal(s) as ESA's, and violations of the Fair Housing Act are very expensive. 

This give you the option to do a home inspection, and release if its bad, but ensures the sellers that you won't be asking for a laundry list of items.

That before you form the LLC in the area you plan to invest in, you need to ensure that LLC for the specific stare has external asset coverage.

always get the insurance binder to protect yourself from loss.That's what I would expect from this scenario, but I'm still fairly new to the lending/note space. 

I know him well enough to assume that the price he'll give me will probably be a very fair one. 

Now I'm working on filing but it's fairly complex tax situation with multiple companies I own in multiple countries over a few years so it will be a bit before it's fully sorted...

I am not fully convinced on  such 3rd party software  Fair enough, have you had any luck with software which you are manually uploading transactions?

But I'm trying to work it out in my head how I can ensure I don't walk into a mess.

The thing I am noticing though, is that these properties are still being bought by others in the area, fairly quickly, close to asking price.