@Michael Blackwell great information, yeah the challenge with house hacking multiple bedrooms is finding our own privacy...but I understand that the basis of a house hacking strategy is temporary inconvenience for a long term benefit! 

However, I'm going to start looking at it soon based on the whole "core-to-shore" program going on.

Baldwin County is a seller's market from the Eastern Shore down to the Gulf. 

It is right on the shore (not beach front) about 3-minute walk to the beach.

Flipping right now is extremely hard, almost impossible in this area, the only reason you might be able to make it work is the fact that you are a contractor, I’ve found D.C.proper  to be far the easiest of any of our area’s to make flips work, the issue is the price is still quite high (usually 500k plus and then a 200k plus reno) the other area that does occasionally have some flips and almost always has some value add, though often it makes more sense to keep as a rental since your selling costs can eat up any profit, is the eastern shore of Md. it’s definitely really a tough market for flipping right now though and I’d strongly consider just getting something turn key or a mild fixer than you can rent out.

I renovated all the work the city inspector asked me to fix on the temporary CO, but I did not close the permits.  

Here is how we addressed it at the time: (We needed a temporary situation to seal off a room for a 12 months lease. )With our method when you need to bring back the door way, you will only have screw holes and painting to do.

The reason I'm posing this question is because I have a deal in the South Shore of Massachusetts (Weymouth) that needs "real cash" to close.

Do you happen to know the regulations and permitting requirements for the North shore near the stadiums?

We closed on a two flat in the South Shore for 60k.