Freddie has similar intricacies, but also does not require a two year history of receipt; https://guide.freddiemac.com/app/guide/section/5306.4If you can use the rental income to drive the DTI down so that you can reduce the down payment similar to that of the FHA product, the benefits of the conventional option will outweigh the FHA option, as I'm assuming you have a strong FICO based on rate quoted with no points.  

• Is it all just customizable based on what works best?

Free vs. membership based. 

Property values have been appreciating rapidly in recent years, and the city’s population has started growing again—a trend we haven’t seen in decades.I’m also based in California and have been investing in Detroit for several years, so I understand the concerns of out-of-state investing.

Quote from @John Lee: Hi all,My name is John and I'm a recent college grad about to start a Masters (SF/San Jose Area home base in California).

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

I wouldn't pick a random market far away based solely on statistics or numbers.

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

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?

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.