Also something to consider is what is the appreciation play looking like? 

It's essential to verify if your property falls within such a mixed-use district.Special Authorizations: In M1-2D districts, residential uses may be permitted by authorization from the City Planning Commission, subject to specific conditions and bulk regulations.

The big boys play this as a team sport, so think about what you need to know, who you can get it from and then go find that person.

nice job I grew up flipping land I love that play still fund land flippers to this day is a niche of lending that I have carved out.. 

Together, they have a lot of units in play there and have done very well with long-term rents and mid-term as well.

Selling now avoids capital gains tax and lets you reinvest into a new primary home and a solid rental property, which feels like the safer play given the cash flow challenges and ARM timeline.

Definitely go the legal route here, don't rent out the basement unless you have the OK from the relevant authorities--it's regulated for a reason (fire safety, carbon monoxide poisoning, etc.) and your insurance will not have your back if something goes wrong.

The STR, if purely an appreciation play,  is speculation to me. 

Most gulf front investments are mostly appreciation plays unless you do a serious renovation.

It's good to hear that you want to play the long-term hold game as that is how you'll ultimately build equity.