I am honestly not sure what the best course of action is in this situation, but I just want to say that you are NOT an idiot.Did you have any sort of written agreement with the PM company when you purchased?

If you or CPA needs a AMA shoot me an email and we’ll get you all sorted.  

Part of my issue was not having a reasonably priced handyman ahead of time and eventually overpaying to just get it done and also inexperience as a manager.With that said, you essentially have two options: very cheap properties in less good areas (you're looking at 100k or less--which you might have trouble getting a good lender for)  or trying to do some sort of house hack (e.g. live in flip, live in rent by the room, multifamily) where you budget will be closer to 200k-300k.Personally, I would not look at real estate until you are maxing out your 401k and IRA, but lots of folks have done significantly better with real estate than stocks and would think I'm crazy for suggesting this.

I think there’s some sort of option of to do a little refi on both house 1 and 2 and get the money needed to wipe out the line of credit(allowing for bigger flip opportunities, especially if I partner up with someone) and also renovating that garage space with the private investor as long as it is under 1000/month.

You need some sort of insurance that covers non-owner occupied properties, whatever it might be called.

The seller isn’t an individual, it’s a company that engages in all sorts of real estate activities.

I have $25K cash for a down payment and can add $20K/year ($1,600/month) toward payments.No W2s, I've looked into building a small home right away and using a bank statements loan (have about 8800. monthly income) , but with 9%+ interest rates, it’s beyond my budget.Is there any sort of creative financing ideas possible or private lender possibilities?

Sell too soon for tax reasons - and pull your hair watching this investment climb up while you no longer own it.Harvest investment gains or losses.

As I said usually when companies cant cut checks right away its some sort of cash flow issue.

Learn how to evaluate a market by either reading and listening to a lot of content or by providing some sort of value to someone who already has that knowledge.