I’d really appreciate the opportunity to learn from those with experience.

You will learn the most from first-hand experience.

Your decades of experience have made you jaded. 

Do you have any experience with it?

If I may, in your experience, is this difficult to accomplish with a HELOC already established?

@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.