I want a broker that is online friendly and no need to go into the office. 

Are you looking for tax breaks and using real estate to offset income? 

I have begun to collect and really learn more about the art of Bourbon and have taken a break from reading books about  Real Estate for a few months to reset a little and have dove head first in to the world of bourbon.  

Take into account it was 12 years ago and he presumably has a clean record since.

You're probably not breaking even, but if your subsidizing the property isn't breaking the bank, then holding onto it and waiting for interest rates to go down might be better.

I'm keen to diversify my portfolio by venturing into real estate.

If an investor loves section 8, this is an easy one to get into.

Should I move out into a house/duplex and house hack?

I don't know if I need a partner, investor, or just more patience... which is why I have joined BiggerPockets and begun to look into the wealth of information!

what it sounds like you are asking is illegal in many ways, section 8 laws, local laws, duel contract laws that conflict, there always has been also those out there looking to catch you breaking them,  avoid it, dont offer it, dont entertain it, there is leeway up if the tenant meets certain conditions, say need 1 floor rental, if not rent may be inflated over realistic market, which is what rented at not listed at, keeping in mind sec 8 market rents also include utilities paid, you can usually reach by email fastest, they have set chart, heat type, neighborhood etc, more than listings found online