Once I reached that goal, the drive for the next one felt just as strong.Reminder to enjoy the journey and that it’s not about the destination.Every goal you reach, you will enjoy it for a short time, then be on to the next one.How do you balance striving to do better and for more while understanding that it will never be enough?

I have owned 4 short term rental in those markets.

If you're allowed to object and you're still within your objection period, you may want to review your title commitment for objectionable matters that may give you a right to terminate without penalty.

Even in 2008 home prices slightly dipped about 16% or so for a short time.  

Since you’re planning a mix of long-term and short-term rentals, keeping detailed records and setting up a solid system for managing finances early on will be key.

Move on to finding a credible/chaos-free tenant.Such a short, succinct reply.

More insurance will cancel short term rentals.

.—(1) Whenever money is deposited or advanced by a tenant on a rental agreement as security for performance of the rental agreement or as advance rent for other than the next immediate rental period, the landlord or the landlord’s agent shall either:(a) Hold the total amount of such money in a separate non-interest-bearing account in a Florida banking institution for the benefit of the tenant or tenants.

The appreciation and annual rent increase could give a good IRR with a reasonable holding period. 

Understanding STR regulations in a market is an essential "must do" when it comes to evaluating a short term rental.