Time to buy? Time to sell?

[Brian Langstrom]

From a prior post, I am newly single. I was trying to partner with the ex and it was not going easy. So, I made the move and bought her out. Best move of my life. Not hard to do and with creative financing, my mortgages only went up 15%. 

Now that I control the equity, I am trying to decide do I sell them at this peak price time and hold till the next big drop? Or do I buy a couple more dup/tri properties? I have three nicer ones at a newer low price that might work. Tried the Airbnb last season and the property damages just make that impossible. 3am calls because they plugged the toilet and why is this wall blue, just not worth it. But I am signing on with the Visiting Nurses group and that looks promising.

Thoughts on what to pursue in Naples, FL. Kinda worried on STR even for season. Marco Island just made them impossible to deal with. Will Naples and Collier County follow that same route?