This is not going to be the best advice for each and every investor in every state, however, generally speaking, it is the best entity to flip from.

Hi- can someone speak to requirements by city to do either short term or traditional rentals? 

No one that has ever tried to use a home warranty for a repair speaks highly of them. 

Generally speaking we target properties that are $250k and lower.  

Generally speaking yes.

I know you're not going to like this answer but you may need to speak with a good CPA. 

I am just south of you in Florence but at least down here there are no rentals to speak of and they go fast, if you can't get it rented by Sept 1 there is a large problem you need to look into.  

You can use the VA loan again, but your entitlement will be reduced as long as you still own the original property.  

The 203k might be a good option but make sure the lender you speak with offers the 203K Full AND Streamline version AND the Fannie "HomeStyle" loan as well.

Some offices will hold tenants responsible for their items (like smoke detectors were there on move in but magically they are not there on the yearly, clearly a tenant issue) but generally speaking they hold the owner responsible no matter who actually caused the problem.