I think maybe a co-sign with someone like my parents would be ideal... also any insight on Multi-Family homes in the Hampton Roads??

However, I am not currently employed, so I was hoping to use a co-signer to overcome this hurdle.

Cash flow will be better on suburban 2-4 unit properties, but your appreciation potential will be lower, as it's relying primarily on rent increases to drive appreciation in the underlying asset.3) I would speak to a local RE attorney and have a co-buying operating agreement drawn up.

The purpose of a co-signer is to give the lender some security should the primary borrower's circumstances change and can't make the payments.

I went thru being a co trustee when my dad died.

Underwriters will likely have an issue with how your income is pieced togetherI’d recommend trying to find a co-signer to go along with you on the loan, or look at commercial/non-conventional lenders who will qualify the unconventional income you do have

At the end of November, I rented my 5 br, 4 ba rowhouse in Washington DC to HubHaus, a co-living startup.

I would not be getting any cash flow in this situation or plan on selling it at least for a very long time.Also, I have the best credit, most money saved and best debt-to-income ratio out of my 2 siblings; should I sign as the borrower or a co-signer, and does that make a difference?

It's likely you won't be able to get a CO after vacating, which you need for Airbnb. 

On the upside we have access to a co -signer with a good credit score.