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

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.

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.

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.

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.

DIY A first-time DIYer can expect to spend several hours replacing a kitchen faucet.The time it takes depends on your experience and the faucet's complexity.You'll need tools like wrenches, a putty knife, and a small bucket.You'll also need materials like supply lines, silicone caulk, and plumbers tape.You may be tempted to be cheap and estimate only 30 minutes, but you should estimate an hour to be safe.What about the time to go to the property to figure out if a 2-hole or 3-hole faucet is needed, then drive to Home Depot to get it, drive back to install and then head either to the next job or back to the office?

I'd love to connect further and hear more about your experiences!

Adding an ADU: With your dad’s construction experience, building a 2-bed/2-bath ADU could significantly increase the rental income.