I have a relationship with my bank for 30 years and they just denied me b/c my DTI is 49. 

Also, what are some of your preferred neighborhoods to invest in (A, B, C)?

I've since sold off most my low income properties and in A and B areas.

My most successful SFH investments have been in what I would say are B-/C+ neighborhoods, and I'm looking to continue this with multifamilies.

The market value of the house is 285000 and it's in a B neighnorhood.

From an economy of scale perspective, it's much more efficient for me to go over this stuff with a room full of accountants (I notice your title :) since typical consumers have no idea what's on their tax returns, or any of that, but the pushback you get if you're me is a) the general low-level animosity between mortgage and tax professionals and b) the notion that I'm trying to "tell them how to do their jobs," which they are not interested in.Far from it on b), I'm not qualified to tell you that at all.

So, I'll soon be moving to Indianapolis and I want to buy a decent house with the intent to air b&b the extra space.

B) lets you understand the importance systems and how they help

The 7th unit I would air b and b to see if there is any interest.

It's important for HOAs to have Super Liens b/c it jeopardizes the entire complex if they do not collect.