Larger house outside DSW resort or smaller inside resort for STR?

[David M.]

So I am new to investing and have been reading materials, listening to podcasts on BP. I would like to purchase a STR in Kissimmee, FL area. Originally thinking 4 BD 2bath min, with pool. Willing to spend on updating/upgrading the interior as needed (and reasonable). Question is this: From an investment perspective, is there better chance of success (keeping "some" positive cashflow) owning the above property in a resort community with high HOA's or a larger 5 or 6 BD with more sqft in the same zip but not in a resort, low to no HOA?? I am in Bay Area, Ca so would hire a local management company.

It seems larger houses bring in more cash but I am not comfortable yet with occupancy rates since AIRDNA, Craigslist, ... seem to be very different.... 

Thanks in advance, any insights will be appreciated. 

Dave