Would start there/check that out!

Casey Check out this article published on BP last year on this exact topic - https://www.biggerpockets.com/blog/brrrr-loans-what-are-the-...A couple of more notes:-The 12 month seasoning thing is likely due to the new conventional (Qualifying Mortgages - Agency Fannie/Freddie Rules) that rolled out last April making this the standard rule for conventional loans.

I even checked in Cross Property Search to make sure these aren't being advertised in a different category. 

Do  background checks work for out of country people?

Also I would check the return on investment, if you were to make those improvements.

Before you make your decision, check  Furnished Finder to see what the competition looks like and how many have wide open calendars to get a sense of supply & demand.

Is there a way to accurately evaluate the repair cost of this kind of issue? 

Check in with @Joseph Chiofalo for construction loans or construction to permanent financing.

A Self-Certified permit review would likely only take a few weeks; as compared to 4-6 Months for a project which is not "Self-Certified" and needs to go through the "Standard Plan Review" process.A Zoning analysis should be performed for your property ASAP using a Plat of Survey to ensure you would be allowed to build what you want to build, and check for any potential "Setback" concerns when it comes to adding Dormers...

Check out my personal favorite, Set For Life by Scott Trench , or The Total Money Makeover by Dave Ramsey.3.