Narrowing down major markets and condo vs single family STR?

[James Oman]

Looking for advice on a few topics. Wife and I are starting to look at investing in our first short term vacation rental. From Minnesota and looking at a property on the Gulf Coast of Florida, likely Clearwater/Tampa or Emerald Coast. 

1. Couple areas I'm having challenges with is any advice for narrowing down a larger metro from one another? I'm more familiar with Clearwater from past vacations but the limiting of STR's gives me concerns as a first time investor. Not as familiar with Emerald coast region but everything researched seems to show it as a great place to invest.

2 We’re looking at $350-425k budget to start but could probably get up to $475/500k if we felt it was the right property. Any advice on starting with a condo/resort type property over a townhome or single family home?  We would like to be as close to the beach as possible with least amount of maintenance or flipping simply due to being further away. 

3. Last question, with housing markets as busy as they are, is there a better time of the year when more units come on the market? Im anticipating a bidding war but am I wrong to think end of summer and fall is when more people would start listing?

Sorry so long but appreciate any insights!

James