I own my own businesses though.

Until about 2 years ago I owned a custom wheel company that built one off wheels for high end/race cars.I currently daily drive a 2005 BMW 745i, trying to decide what to replace it with.

At least, if you advertise each room separately, you're placing people in a house who might not have otherwise found each other and can get a house more affordably than they would on their own.

We do provide our own EMDs and Transactional Funding. 

While I don't own a brokerage, I have been managing a team of RE agents for over 5 years. 

Every lender will have their own method/calculation, but most lenders will assume some amount of a minimum payment and apply that in your DTI calculation. 

The you simply restart the process by being your own bank and reaping the benefit of getting the best deal since its an all cash offer.Even if you do have a great rate on the first its holding you hostage on your equity and there is a way to beat the rates so you pay less.  

The advice of the prior two posters: "speak to your CPA" is spot on.If you are investing in syndications that have activity in states outside your own, your tax situation is sufficiently complicated to onboard a professional.

I'm a new investor (2019) with 2 properties (1 SFH solely owned and 1 apartment building, co-owned with family) in the Bay Area.

But if I had gotten my tail into gear at your age, I would probably be typing this from a cabana on my own private island.