Picture the BIGGEST graveyard in the world, stretching as far as the eye can see, horizon too horizon.

Instead of throwing your deal out to a bunch of strangers on the internet, I recommend you do your research to find a local expert with 20+ ACTIVE years in real estate in your market.

Also, dont work with big internet lenders like rocket, lending tree, etc.

While your lease may indicate that the tenant pays, the biggest problem with this is that tenants will stop reporting issues for fear of paying.

But by the the biggest issue is PRICE.

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

The biggest difference to me is that YOU have control of every aspect of an active investment, while somebody else is in “control” of a passive investment.  

I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

My local cable, internet, cell and utility companies are already using it to field calls and answer questions online and phone.

HOA fees, in particular, seem to be the biggest hurdle.