Your decades of experience have made you jaded. 

@Walter PinedaEven if someone give you a referral, what meets their expectations, may not meet yours.In our experience, the #1 mistake owners make when selecting a Property Management Company (PMC) is ASSUMING instead of CONFIRMING.It's often a case of not doing enough research, as they don't know what they don't know!

If there are any owners on this forum that have any first-hand experience with STRs in the Kissimmee area?

Unlike cash buyers or those with extensive experience in the market, many younger buyers are still navigating the mortgage process while actively house hunting.

It will save you a ton of money upfront and you'll gain the experience to upgrade to larger deals.  

Finally, start small, analyze deals, and build a team to guide you as you gain experience.

Given you and your investor both have experience in different areas, I’d say keep a flexible approach and compare city requirements before putting too much money down.

I have met a few folks recently who are active in that market and I am planning on following up and seeing what their experience has been.

You'll likely need a higher down payment if you can find anyone willing to finance something like this as a first time investor; many require some level of rehab experience at the very least.

I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.