So I have been having a lot of trouble getting a cash out loan on one of my properties I own outright, and I thought DSCR lending was going to be my saving grace.

W2 jobs do NOT qualify you for Real Estate Professional status, even if the job is in real estate! 

I'm wondering if I can qualify by using just 1 or 2 bookings (under 7 days of course) for the year.

Hi Jim, if the property isn't being used as a STR currently, certain DSCR lenders can use data like AirDNA to qualify for financing.

Get pre-qualified for a loan and look for a multi-family to purchase instead of a single-family. 4.

660 and above should qualify you for DSCR. 

I want to know if this type of business qualifies as a “real estate professional” status.

You only need 20% to qualify, along with a credit score typically north of 660.

Vet some PMs, tell them your situation, and get a very qualified one to get you out of it.Going forward, either learn how to detach yourself from this nonsense or enter an asset that does not require human interaction.

Not an issue for everyone ( mine is 800) 3 For down payment  there are  down payment savings plans ( I have an IDA) In addition there may be additional 1st time or income qualified grants available  ( in my area its up to 60k- if the funding is avail) Also non IDA savings and gifts ( from what I hear) could be used.