They want to get a monthly check without having to work for it.

Get an estimate from a GC to get a good idea of what is required.Market Comparables: Check what similar-sized homes with finished basements or additional bedrooms are appraising for in your area.

Each programs have different requirements so it'll be important to check.

Check with your tax accountant.

I wonder if they’d be willing to just send me a check for $13k/mo?

Because instead of collecting one rent check per month, you’re collecting multiple payments from different tenants.

Check with your broker for guidance.

It took us a couple of weeks but we slowly increased their rankings unit they were on page 1 (based on search parameters of course) and they got a 10 day booking soon thereafter.We use Price Labs to check out the date of the last booking.

I use problems like this to go an check out the problem and then the entire property while I'm there, looking for other problems, but also assessing HOW the tenant is taking care of the property.  

These are non-standard setups.