My main concern is that I would have to find local housekeeping and maintenance folks and coordinate cleanings/fixes between checkouts or if the guests have any concerns while they are there.

We could live at my parents home for a year (it is their vacation home not their main home).

Another reason is that we have basements with wood subfloor in the main living space. 

I hope to return to MA in the future to grow my business and my family. 

Eventually, once I can make real estate investing my main source of income, I'll probably move to a better tax state. 

Main reason to go FHA over conventional is if you are unable to qualify for conventional, as FHA does have more leniency.

The main ridge is probably stable but the porch ridge is not.

Investment Info:

Single-family residence fix & flip investment in Wells.

Purchase price: $384,000

Cash invested: $15,000

Live-in flip property. This is my primary residence but we've been updatin...

Volume I focuses mainly on small multifamily, which sounds like it would be most beneficial to you.

. - it's a lengthy answer.Check out the city's main site that also links to supplemental content: https://www.chicago.gov/city/e...Also, here's a BP thread with some Chicago architects weighing in: https://www.biggerpockets.com/...