This lowers the chance of triggering the “due-on-sale” clause.Consider a Land Trust to transfer ownership without alarming the lender.Once transferred, use the LLC’s account for all rental income and expenses to keep it separate.This post does not create a CPA-Client relationship.

I'll use that to estimate the ARV.

Then do estimate of the repairs.

While you may be trying to do the right thing, if you buy the house from them below market and they find out later on chances of you getting sued by a pro bono attorney is very high.

I agree with @Chris Seveney that he doesn't have any chance of fixing anything with a custodian and needs to focus on making sure tax returns are correct and assets are moved to his personal name. 

This would give you more legal standing if they don’t leave on time.Walkthrough: Ensure you do a thorough walkthrough with your general contractor once the seller is fully out to assess any new damage or necessary changes to the scope of work.Planning ahead like this will give you peace of mind and reduce the chances of things going sideways during the transition!

Hey @Chance Lee , I personally have Airbnb and other OTA's remit all taxes to me.

“The rents increasing, high unemployment during Covid [and] the reliance on the rental assistance have all kind of culminated in what can be a difficult situation for some of our residents,” said Courtney LeVinus, president of the Arizona Multihousing Association, a landlord trade group.Still, Torres estimated that a third of property managers in Dreamy Draw had abandoned lenient policies this year that allowed tenants to sign promissory notes, giving them more time to pay off owed rent.

Then you'll just have to take a chance and find out.I have my theory about who succeeds and who doesn't and I'm working on a Blog to explain it.

I am wondering if it makes more sense to just deal with the large upfront cost to have the roof done fully or if repairing the damage will end up coming back to haunt me.It's a rather small house at just over 600sqft, for an addition is it really just a matter of getting estimates for the addition and comparing that to the additional rent I would get and seeing if it's worth it?