Alternatively, I was considering bridging the two units and converting it to a luxury family residence (neighborhood does hit million dollar homes) but not sure if the market will support the price tag (this part is easier, and I think the fact that the current owner who claims to be an investor himself yet hasn't made it work... this tells me it probably isn't favorable towards a flip). it definitely is not favorable as a duplex rental so the only way i see it working is to add doors.

But never forget, complainers are going to complain.Have the crew drop off a pastry / coffee or a nice lunch from time to time, that works wonders too.  

It shouldn't be an issue, there's nothing particular about what you've posted.

Direct deposit to your account can be an issue for problem tenants (partial payment is tough to stop). 

We tried to over-provide and had things like both a traditional coffee maker and a Keurig.

Hit up local coffee shops (or find out if any exist!).

What you are describing is most likely going to have to be an off market deal.

Although with lesser of a budget and capital to work with, this wouldnt be an option. 

If necessary, I'd consider a mortgage instead of a HELOC, but that would be an inferior option. 

Not saying their won’t be an impact as the economy worsens but not as bad as other areas in my opinion.