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.

(Ironically, I'm sure a good portion of the people arguing against development are also upset with the government for not tackling the affordable housing issue.)If I were WIP and felt I just got cheated out of my right to develop that land, I would have put a fence around it. 

I like new homes in up and coming neighborhoods because there usually are fewer maintenance issues and can you usually get higher than market rent.

I've also heard it can be a good thing to have some debt against a property because if any issues arise legally, the bank will be the first line of defense. 

In my mind if you have these issues if I was the seller I would let  you cancel and get your EM back  not your inspections and other things but EM yes.

Plumbing company says its the only way to resolve the issue I have.

Either1) your startup takes off and you can distribute profit fast enough to pay off your debts, or2) you find another source of $100,000 a year (which barely even starts to pay down the $300k, but might provide a better chance for a better loan), or3) you BK and possibly lose the rental houses to creditors (hopefully not, but we don’t know how they are held), or 4) you sell the houses, take the tax hit, work with the IRS on a payment plan whose interest will be much lower than your CCs, and focus on the startup.  

Good news is our land is where all of the next-door houses are (free houses, I think legal issues). 

If you are a control person, this can be a challenge but I have learned to let go over day to day issues that come up that I would do differently.Handypersons are a tough one.

I invest locally and invest out of state, and the main issue for most is the shiny diamond syndrome providing you the reasons why investing (insert area here) is the best place.