•If you purchase a multi-unit property next, rental income from additional units will help you qualify for a larger loan.Final Thoughts•If similar homes are sitting vacant for months, it may not be the right time to convert to a rental.

Courtesy of Dodd Frank, its doubtful the self employed will ever be viewed by lenders as favorable as a w2 employee.

You have to be super cautious though when looking at opportunities since some may come with unexpected circumstances such as major repairs, fines for illegal units, etc.

I despise units that are older where sound travels easily or also units that have either more units above and below.

"Wholesaling", where you only find the deal for someone else and don't close on it first *your own self* is selling real estate and requires a real estate license here, and in many other states.

I have one rental property that I have been self managing for about 10 years but I'm looking to exploring and potentially doing my first Flip this year. 

Is this a single-family home or a multi-unit? 

I am interested in living in the basement, and renting out the upper unit on Airbnb.

Moreover, I would recommend prioritizing a W2 position over 1099 self-employment/sales for two reasons.

While you may always have a skip, early termination, or eviction, spreading out the lease-end dates can help avoid having all units vacant at once.