Quote from @LaShon Evans: I manage 400 rentals and own 33.

. - Has accumulated tens or hundreds of thousands of dollars- Has a thesis to purchase extremely distressed office buildings in urban locations, get them re-occupied, self-manage and work in and on the buildings to get them re-rented, preferably Denver.

Quote from @Jacklyn Robins: You've "never" had this issue, but you've only managed a few properties for five years.

I think both of your strategies have merit, but here’s my take based on what you’ve laid out.Moving to a rent-stabilized apartment and renting out your condo as a mid-term rental could be a smart pivot, especially with its location near a hospital and LGA.

It's all the about the location and the view.

A major part of the success or failure of an STR investment is the design, furnishing and management plan.

I’m open to exploring those locations since they aren’t too far of a drive.I’m leaning towards a SF property because I have $10,000 to put down, want to stay within my budget, and being new to this, I’d like to start small.

You need to work with a property manager that has experience with this, unless you plan on doing it yourself.

While I have managers handling the daily operations, I still oversee everything remotely.

That’s great advice Taz, I’m currently working on saving enough money to get started, house hacking is hard for me at the moment because I just bought a house 2 years ago, I would have to sell my house(which is in a great neighborhood great location) and use that money to fund the duplex which isn’t totally out of the question, I would like to keep the house if possible but also would like to get real estate investing more.