Market is difficult, I see much cheaper deals from wholesalers in the Tampa area than down here lately

This is due to the difficulty making a profit with the heavy overhead, including high management fees (ave 27%,) high repairs & capex from harsh winters & sun at the high altitude and wear & tear, snow plowing, expensive insurance and some of the highest utility costs in the country. 

How difficult is it to get a 75% LTV cash out refinance?...

How difficult is it to manage vs just the pool for guests?

Some counties and Cities are more development friendly...but some also have more difficulties.

Florida is only second to California with difficulty acquiring a contractors license. 

Is the city approving new STR permits and if so how difficult is it to get them approved. 

I never recommend selling a house unless you are selling it to invest the money in something that provides a greater return, or you are experiencing financial difficulty and can't get out of it through other means (e.g. a part-time job).Have you considered living in the 5bed house and renting out a couple of the spare rooms?

I sent you a PM as well, but the difficulty I have had when looking at these kind of projects (at least in my markets) is getting an accurate quote on what the total cost will be. 

I'm having difficulty keeping my wife focused on flips since 1% deals are easier to find  than 70% Rule deals in the areas that we like.