This essentially deterred my ability to scale my portfolio.

Also, you can find local vacation rental companies in just about any good STR market who should have the ability to give you market level data.

Depending on what you're going to do with the cash and your ability to pay off the HELOC, it might be worth looking into.

My company is new so I'd have the ability to change it without much trouble.

I used the rental calculator on BP to determine the rents for both units, then just combined them.

What criteria do you look for when someone has ability to buy through a traditional loan?

So nothing should change since your value is based on your buildings ability to produce NOI

Finally, in situations like this, where Bob is taking the loan solely, is a common selling point to Bob the ability to do the same thing as I mentioned before with taxes in order to offset his DTI based upon the income the property produces?

It sounds like your goal is cash flow, along with the ability to snowball into further investments.

I’m looking for good up in coming neighborhoods (C+\B-) that offer the ability to cash flow.