I own a home but know that the journey ahead of me is entirely different.

It's like choosing between two different adventures.If you sell the land, it's like getting money quickly to buy something you really like.

There has always been talk about Grays Ferry for as long as I can remember as being the up and up for different reasons with no action. 

Here are a few points to consider:Risk Tolerance: Real estate and stocks have different risk profiles.

If they want to put limits on future contacts that is different than passing a law that changes a contract between 2 consenting, competent parties that was legal when entered into.When rent control is first passed and applied to existing leases, the government is changing the contract.  

Insurance costs are also a bit different, but at the end of the day, the home was a better option.

Thats a $22k difference between me paying a upfront fee and a success factor.

I have received 3 different but similar explanations from tax professionals.

These all have different requirements.

One is an MTR where we rent long term for 6-7 months then becomes an STR for the summer - the ring camera stays and so far no one has asked anything about it.LTR may be a bit different.