I heard the servicing company laid off most employees and transferred the loans to another servicer (in some sort of agreement).

My experience has been that purchase transactions where the buyer has no or little skin on the game have a default rate many times that of buyers who place a significant down payment into the deal.  

If the costs for home buying goes up for first time home buyers then the results will probably be that less starter homes will be moving in the market unless non profits and the sort step up.

That sort of difference in expense with turnover/vacancy means that the approach to tenant retention means something different to the business.

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

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

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 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?

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.