Would it be a bad idea to buy a single family home built in mid 1930's?

Why would anyone start the purchase of a property, having zero idea if they can actually execute their business plan? 

I think a new administration brings new ideas and new people.

I am very new to this idea, so it's possible that one of these options just doesn't make sense.

Yes, one approach is to continue with finding other cash flowing property.Let me suggest some other ideas for you to ponder, especially since you've also mentioned you are looking hard at DST's:What about Opportunity Zone funds? 

(Cash Flow is my goal) Pros/cons, other creative ideas?

It's usually a very bad idea to go into business with friends or family. 

I’d love to connect with like-minded investors and learn from those who are navigating this market.For those who said they’d like to connect, feel free to reach out—I’m excited to share ideas and experiences!

They were super slow, had literally no idea how to read a basic purchase agreement contract, messed up on most of the paperwork, and ultimately were going to cause us to close 2-3 weeks late, with a lot of extra fees and less LTV than originally promised.

I have NO IDEA.