Even if city looses, they'll probably make things difficult on operators with all kinds of rules and regs like many other cities. 

Tip #1 - no such thing as one perfect market There is lots of data on Bigger Pockets and MTR experts that have released rankings of top cities for next year, but remember it's not just about the purchase-- it's also about the operation.

Aside from that, it sounds like my operation is quite a bit smaller than what you and your network operate with, but properties that are wholesaled are usually all cash or hard money, so the initial funding aspect usually isn't a roadblock.

As an appraiser I’ve appraised a handful of properties recently that are outside of city limits and operating successfully as STR’s that don’t have the same regulations as the city of St Pete.

All in, I think a large amount of GC's in the residential world tend to operate in less professional manners, which results in a lot of the problems we have read and seen above.

While the second LLC does not yet have an EIN, can we temporarily operate using only the bank account of the first LLC (which also holds the property)?

She's not trying to be an airbnb operator.  

Hawaii is one of the two markets I operate in (and Anchorage, AK).

Also her husband has 100 acres of Teak and I wanted to see their operation. 

Quote from @Chris Mason: They have simulators for heavy equipment operators: bulldozer, backhoe, etc.