First vacation rental property, thoughts and advice appreciated!

[Andrew Royce]

I currently live just outside Cincinnati Ohio and have 2 rental property condos. Im looking at buying my first vacation rental condo and am leaning towards St. Pete, specifically the stretch between Madeira and St. Pete Beach. 

So first question would be any advice on those areas? Hoping to be walking distance to beach, restaurants, safe, etc.

I'm also struggling with cost analysis for these properties. With my long term rentals here it's fairly simple, you have taxes, HOA fees and insurance but with a short term rental i'm not sure how to handle VRBO fees, vacancy with a short term rental, out of state taxes, etc..

Still fairly early in the planning phase but have to start somewhere so any help is appreciated!

[Andrew Royce]

Appreciate the info, especially on the short term regulations. Something I will look into more as I continue my research.

As for financing, it shouldn't be an issue as I'll have 50% or more to put down. Both my properties here were either foreclosure or purchased without realtors. Because there are more costs associated with an out of state rental, I'm inclined to go the foreclosure route as the purchase price is really the only large variable that can determine if I'm going to be cash flow positive or not.

@Tyler Work Thanks for the offer, Im going to do some more research but will hopefully be in touch soon