However, with high confidence my old property will sell quickly in my current local market it is well worth getting into the next property quickly if the numbers make sense based off the new mortgage.

As I'm only truly exposed to my local market, I'm curious what people think is the most undervalued major market at the moment compared to 5 years from now and WHY. 

Find a local meetup and go to it every month at least.

Hey @Eric Forsberg I am always looking to connect with local investors.

ive been mostly looking for conventions but everything ive found is along the lines of "Grant cardone featuring david goggins panel; buy your tickets for $400 and network like never before" - anything more aligned/tailored for local investors? 

I also have local resources and references I can share. 

I'm an active Realtor and investor and on the board of our local REIA.

If they are insuring the property in its current state, it's likely that a new buyer will also be able to obtain insurance without trouble.As for the mortgage aspect, the key factor will be ensuring that the house, including the patio "room" and its roof, meets all local building codes and standards.

Look up your local rules. 

I know some state and local governments have laws on STR and of course thats a important factor.