We were okay with paying a bit extra for something we love, but with the added complications of the undisclosed claim and the high insurance premium due to the property being in a high-risk status, it’s become a concerning situation.

I personally like to stay in mine for 3 days atleast while I setup to know my properties more intimately and to work out the bugs which would be problems for guests.

We own in Florida, but we do not own in the keys and I was hoping to get some more nuanced feedback than what I've seen in older posts (something more than "follow the law, get STR license" etc).Specifically, in the lower keys (Summerland to Key West):- how important do you find private dockage to be to 28 day "STR" guests?

And it is for this reason why a good REI Buyers Agent is worth our weight in gold, literally, because we make sense and order out of the chaos.

Disclaimer - I am not an CPA or attorney but I became financially free doing this for myself after 10 years working as a w2 engineer :( and I am sick and tired of seeing highly educated and hard working professionals getting stuck in the rat race because we deserve financial freedom and the option to do more with it.If you are able to implement a real estate professional status tax strategy (REP) you can use passive losses from syndication deals to lower your ordinary W2 income.

The owner and tenant attest to the status of their rental agreement.

40+ guests in first 6 months of STR activity - All 5 stars, with exception of 2 4-stars.

We dislike VRBO bookings when the dog group from VRBO, and VRBO hind guests information, change an email to be a new guests so bad review will not available,  and felt 0 support for hosts.Thanks to share your experience.

I recommend spending a couple nights in the unit so you have the perspective of a guest to notice anything you are missing or need and develop a check list for your cleaners and/or property manager.Your agent should be advising you on all of this and more and have local contacts for you. 

The three tests outlined above are applied annually, so you may qualify as a real estate professional in one year and not in other tax years.It is also very important to document material participation.To meet the requirements of real estate professional status, it’s essential to keep detailed records of activities and time spent working on the properties so you can verify your real estate professional status in the event the IRS decides to audit your return.For example, you may keep a contemporaneous appointment book, calendar, or narrative summary of the time spent performing real estate activities.