Based on your description, Party 1 seems like the safer choice.

I also have rentals in Detroit that I get far higher rents with cash paying tenants than I would a section 8 tenant.There are a lot of factors at play and the answer to "why would the government allow our tax dollars to be spent this way?"

If you are trying to come up with a way to finagle the occupancy requirements while using an amazing loan (that you earned based on your service) like a VA, I would say you are starting off on the wrong foot.

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).

This is the foundation of why LaPlante Real Estate is based in portfolio management and property management... my personal portfolio started in 2009 and I find the majority tends to be Section 8. 

There’s just not enough ADU supply (IN MY AREA) for appraisers to base off of.

Just by having those two traits they are in the top 25%, based on my experience. 

I’ve been manually scouring Zillow/MLS for deals, but it’s time-consuming, and I’d love to streamline this.2.Has anyone experimented with using machine learning models (like classifiers or regression models) to rate properties based on their condition from MLS listing photos?

Yes, there are times they do win and make money, but not on a frequent bases in my experience.  

To evict a tenant based on a lease violation such as hoarding would require you to notify them and then give them an opportunity to fix the situation.