I like the idea of unincorporated areas and did so with my first STR, but county wide regulations can wipe that strategy right off the board. 

We are aware that Blowing Rock, Boone and Banner Elk have regulations so we are hoping to find a lot that is outside of their regulations but close enough to allow STR's. 

I'm familiar with WA, CA, OR, FL, NY, CO being quite challenging permit environments, where else in America matters? 

But San Diego is now regulating STR's and trying to force only 1 unit per owner (or 2 per married couple), if you're lucky enough to get a license at all.

It cannot be stressed enough that real estate professionals should always be well-versed in their local market’s wholesaling laws, rules, and regulations to ensure that their business activities are wholly legal before making any moves of their own.The Pros Of Wholesaling Real Estate1.

Problem is that apparently there's some FNMA regulation that will not allow you to purchase condominiums with a conventional loan unless over 1/2 the units have been sold and are not owned by the builder. 

PS is one of the most heavily regulated cities in the US, best not to game the system, or if you do tread lightly after building lots of experience.

For example, if you only put 25% down on a property that means you are earning an APR of 8% (100%/25%*2%) all of which increases the equity you own in the property.Illogical Tax Benefits – In order to attract investors to continue to invest in Real Estate the government has created a very tax friendly environment for real estate investors.

Is familiar with both Ohio and Florida tax regulations in reference to real estateThoughts/suggestions would be greatly appreciated.

Short-term rentals (STRs) can be very lucrative, but they're highly regulated in many attractive markets.