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

[Wendy Schultz]

I own two properties in Kissimmee and manage another. Contrary to Lucas' belief, you can lose money with property managers but not if you pick a good one. What type of clientele are you looking to cater to? We have a property in Reunion Resort and people seem to seek it out and are familiar with the resort. You can also find properties outside an HOA but be really careful of the neighborhood you select. I was attracted to the idea of no HOA fees and looked at house outside an HOA but then saw the way the neighbors took care of their houses (or didn't, rather) and knew it wasn't a good fit for STR. The regulations in the area can be very different depending on the location so be sure to understand the ordinances governing the location you're looking to buy. The biggest thing I see is that there are a lot of properties in the area so if you can find something unique, that's a better bet than finding something like all the others where the only thing you'll have to compete on is price. Let me know if I can help.