Are you thinking that some software will replace a hands-on property manager? 

Additionally, since you need to replace your vehicle soon, you should consider how that $30k purchase fits into your overall budget.Take a close look at the current housing market in Orlando, where prices are around $400k for decent homes.

Does the 60% the condo-hotel takes include the HOA fees or utilities or replacement of furniture/repairs to the unit like plumbing or stuff like towels and sheets etc?

So you may need to supplement more outside money to the purchase.You can always choose to add cash so you end up owning your replacement property with no debt.

Replacement Cost policies.Basic vs.

Over and over, you can be constantly evicting and replacing appliances and doing major repairs.

Yes, the thermostat will need to be replaced with a smart one.

Let your STR start making money before adding cost in replacing the flooring.  

But you have your health and your family....you can replace everything else.

What I did was after my sale was under contract and I was down to a couple weeks from closing I started shopping seriously and had my replacement under contract a couple days before my sale closed.