Hi Michelle, I don't know about Philadelphia, but there are good markets in the Mid-west.

Wondering if there's any point in looking West towards the Clermont area, but nervous about regulations.

We help roughly a dozen investors acquire STR’s out west annually, my advice to STR investors is to create a home and a space that is yours to share with others.

Here are pockets I focus on for cash flow:West side - West boulevard, Cudell, Clark-Fulton, Jefferson, Bellaire-Puritas, Old BrooklynEast side - Fairfax, Buckeye-Shaker (the north side), Waterloo Arts District, Garfield Heights, Maple Heights, Newburgh Heights, Lee-Miles (the north side), BedfordHere are the areas that I focus on for appreciation:West side - Lakewood, Edgewater, Old Brooklyn, Ohio City, Tremont (above 490)East side - Buckeye-Shaker (the north side), Waterloo Arts District, Fairfax*I have a graded neighborhood map of these areas as well if you would like to check it out.

I live in Key West so a STR or a fix and flip would probably take up more time than I'm capable of putting in.

I too am in FL albeit the west panhandle, and am preparing to make my first investment deal so kudos for asking a great question!

The main hurdle that many of our borrowers face are the income aspect of it, especially expensive markets like the West coast.

Not that much to do, pretty flat landscape, too large to be cute and too small to be interesting. 5 hours to a major airport.If it has to be Wisconsin to retire, I'd rather look at the west side of Milwaukee ("lake country") - it's pretty, you have lakes and at least some hills, 30 min access to a 1.6 million people metro area (Milwaukee) and you are in Chicago in an hour and a half.

Hello BiggerPockets, I recently got the opportunity to purchase an off market property in Las Vegas about 15 minutes west of the strip.

A little further West...Oregon.