I wouldn't limit it to roof as wind and water can damage other areas of the home..what if a window was left open and the interior now has water damage etc...Did you already bind your insurance (likely not if you are two weeks out) So there may not be a reason for them to dictate you get it reinspected. 

If we go by the BRRRR method, we're already going to buy and rehab it, then would it not make sense to just flip it at that point and cut out the need to deal with tenants, home damage/repairs, refinancing, etc.?

Now, if you do decide to pull money from your current home, most lenders would prefer to see some "seasoning" of funds in your bank account.

He's the best in the business    His page indicates he only serves New Jersey.

New but learning quickly!  Looking at a property. If it shows on the deed history, Grantor is a bank and grantee is Housing and Urban Development on a special warranty deed, what does that mean?  It was foreclosed?  W...

I flipped a home and sold it a couple of months ago. 

Your next cheapest option would be to buy a multi-family as your primary home.  

@Jorge Martínez100% of homes break.

We would utilize our investment property in Puerto Rico as a second home or STR.

Purchase price: $115,000 Cash invested: $1,170 Sale price: $199,900 Contributors: Peter Vekselman Partner Driven, alongside partners Julie Muse and Cody, purchased a home on Stowers Road, W Dawsonville, GA, for $115,000 on 08/24/2018.