Holding onto a property merely for tax considerations is a dangerous gamble.But if you want to gamble - yes, selling in a year without a W2 job usually saves on taxes.

I'm a territory manager for a telecommunications company, and driving through the Newburgh NY I forsee a huge upside in this neighborhood.  

Option 2 I have similar response to option 1. option 3: We have had STRs since 1999 which puts my STR longevity in rare territory.  

This results in some seriously dangerous advice for your impressionable young listeners.

I have never worked in real estate and navigating unfamiliar territory has been challenging.

I'm not in imminent danger of homelessness due to unafordable rents like I was, which was my main goal, and since the interest isn't variable, while high, at least I know it's not going to increase. 

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

I think a lot feel as I do, that their home territory is too expensive.

The danger of signing up with promoters of a tax strategy.A lot of times, you hear about a specific tax strategy (REPS, STRs, syndications, 1031s, DSTs, conservation easements, and so on) from promoters who target a specific group of people.

They can be all dangerous and some often carry legal risk.