And if the lender foreclosed on the property a few years ago, but still hasn't tried to sell it, then it could be because there's an issue with title, or perhaps there's a legal battle taking place with the previous owner.

Context: My dad has assorted health issues that limit his physical abilities and does not want to fill out forms or devote much time beyond discussing things with a Lead, reading over anything he’s signing, and sending a check.

One is relatively new and other one is quite old. 

The issue I am facing is that the property is zoned for residential use only, and I am interested in renting out both the main house and the pool house as separate units.

To address this, we agreed that I would work in the business for six months to verify the financials, which so far align with his POS system.My main issue is that at 23, I don't have strong financials to get a conventional loan at 75% LTV with a ~7% rate, and the seller's lack of financials complicates bank approval.

You might run into issues getting financing on it

It has appreciated almost 2.5X of the original purchase price, however the cash flow is typically $25 in the red every month sometimes more with maintenance issues. 

  #1 lots of issues with condos

I buy/sell without regard to other property (except when pooling in a mortgage tranche) so can't relate directly with your scenario, but talk to your loan servicer. they can help. 

Canopy- same issues as others, depending on if 60degree or 90 degree parking.D.