You're also LIVING there when you house hack, so you have to factor in what your "normal" comparable living costs would be. 

Most investors will also take into consideration risk, time invested, control over the asset, the ability to do a cash-out refinance, and other factors.

I feel like NY has the appreciation factor locked down.

My student loan payments are $0, but the regular VA lender I've been working with told me they have to factor as if I'm paying $820/mo!

There are other factors to consider, to be sure, but on that score I disagree.

I tell them all they can stay here forever.

Like with anywhere else: location, pricing and the overall house you intend to build will play a factor in your profits.

I would expect the one in his personal name shows on his credit report as a mortgage and the lender will factor it in his DTI.

The answer will depend on many factors since it is a commission-based business.

And, in having to decide where to borrow funds from (others, hard money, our own equity, our own cash), we went with our own equity because it was the cheapest and most readily available capital.As a relatively new investor (i've been doing LTR's forever), I don't yet have solid relationships with others in order to move quickly with "OPM".Thank you for the advice here.