From there, you could do a cost segregation study on that property which will lower taxes for that year and potentially create additional carryover losses.Always options to keep reinvesting assuming the equity is there to keep playing the real estate market 

Preference is cash-flow, but open to appreciation/equity plays as well.

Your number two is a bit different than what to expect on a short-term rental play.

I think the play would be buying a property that needs some rehab and you can split off a new lot due to new lot sizes and setbacks.

Even though we have good LL-T statutes in place in Florida, some judges play loose with them.

They are just playing with fire, really, but it happens everywhere.

Tenants will play games:1) Leave a minor home alone - no one should enter!

Some carriers offer loss assessment insurance, which can come into play when the HOA experiences a large covered insurance loss, such as a hail storm requiring roof replacement or a fire requiring building replacement.  

This typically comes into play with big banks (Chase, etc) who are buying the loans to place them on their balance sheet.

Quote from @Jaclyn Spinelli: Quote from @Aristotle Kumpis: Are you looking for more of a cash flow play vs appreciation?