The people that are going to get crushed are people that buy assets that have negative cash flow and are speculating/gambling on appreciation.

That is speculation and gambling. 

Basing everything on appreciation is speculation ie gambling.

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 love the thrill.

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.

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. 

I’ve been told house hacking is a great way to get started, but not necessarily thrilled about being a landlord when my tenant lives right next to me.