I didn't realize how long it has been since my original post so here is an update if anyone is interested.

Why would he send you a $13,000 bill during the inspection period, unless I read that wrong?

My dilemma: What type of lender should I be using being that I want to acquire 2 mortgages in a short period of time.

It is structured similarly to a HELOC but meant to be paid off in a short period of time - when you sell your current primary home. 

There probably wouldn't be too many updates to it once I moved in and it's listed for $232k.

Home equity lines of credit come with variable interest rates, and you can make interest-only payments during the draw period.

I will update in a bit, but was just sent a quote for something around $400/mo for more ‘catastrophic’ coverage for two of us.

Have you run any rough estimates of the ARV and costs if you were to update and resell the two homes?

background:  - Mortgage free  - moved out two years ago   - Still furnished  -  HOA fee $100 month  - has an expectation of getting same value of homes sold in neighborhood that have been updated even though his still looks the same         from original build in the 90's

Here are some response rates I can share from my pilot of 371 recipients, which I mailed up to 4 times over a 3-9 month period.