Basing everything on appreciation is speculation ie gambling.

Like any other expert -- a banker, an accountant, or banker -- invest time only with an authentic person that you respect and trust from moment one.  

To me it would only make sense to keep your current property if you believe there will be more price appreciation on this property than another one you could buy with more cash flow, but that's a gamble.

.- Cap gain rates increase is only for incomes over $1M- 1031 repeal is only for gains over $500kNo details on either of those thresholds are yet available, so we all have way more questions than answers.Preparing for something that may or may not happen and has no defined form is a gamble.

I had the capital and I did enough research and I didn't feel like I was gambling.

I had the capital and I did enough research and I didn't feel like I was gambling.

However, this isn’t my authentic life.

I feel like this was a big gamble for the OP because if other STR landlords are irresponsible, the association could stop STRs- but he should be fine if he has to transition to long term and rent a room at the hotel when he’s in town. 

It also would be a weird letter to send to a lot of the duplexes here in town, because most of them are in subdivisions full of identical properties.At this point I think it's basically gambling unless you're committed to mailing the same addresses 8-10 times minimum over the course of several months.

One can sense authenticity and one can also sense lack of authenticity.