It’s from a popcorn ceiling that was improperly removed so now we must do cleanup... 12k to wipe down and remove everything from the condo another8k to deal with the common areas that were affected - does that sound fair to you??

If it was his property manager, it was his responsibility to ensure that he was providing you with the current leases, especially if he knows his PM does not check with him before signing leases.

Drain Maintenance -  Any time the truck or the bikes get super muddy they go to the coinop carwash for a rinse - I'd rather leave the muddy mess at the carwash instead of in front of my house - I imagine those drains have to be cleared out fairly often.Winter:  Looks like you're in TX, so might not be as big of an issue for you, but during winter here in UT those hoses are constantly running to avoid freezing.

So if your CPA is preparing your tax return, they are not necessarily ensuring you are paying the bare minimum taxes. 

This would ensure that you can hold either or both responsible for the full amount of rent for the full lease term.

How do I ensure that the deal is structured in a way where I can get them their capital back after the financing period, and is this something that's typically done? 

One of the requirements for a multi is that every living unit must have independent utility services or at a minimum 1. legal provisions ensure and protect access to utilities for repairs, even if passing through other living spaces, 2. easements or covenants protect water connections, and the VA approves of a maintenance agreement; 3. there are separate service shut-offs for each unit. 

It’s a great house, fairly new (built in 2015) and the neighborhood isn’t bad.

I don't know what would be fair asking, am estimating 400-450k?

If they are VERY professional, they will have their processes in writing as verification that it is enforced equally and fairly by their entire staff. 6.