Since I work pretty hard at my day job and don’t have much renovation experience, I wanted something simple—a rental I could put a tenant in and at least break even.

That's a pretty good margin! 

I am guessing that the vast majority of homes 10+ years old had some sort of water damage at some point, most had probably several.My own home is only a few years old and we had the washer spring a leak and a few years later the RO system in the kitchen started leaking into the cabinet.Seller disclosures are pretty useless in my opinion.

It seems to be pretty much impossible!

You have the means to purchase and intend to offer owner financing (you) to the buyers of your lots.That sounds pretty straight forward as long as you are able to carry the loans and deal with any defaults.I don't have a background in raw land deals, so that's all I got.Thanks for the feedback and I will keep these things in mind as I move forward. 

I'm in Ohio and we see those lower loan amounts pretty regularly. 

Getting analysis when starting out is pretty common, buying that first deal is a huge leap of faith. 

But to start with MF that seems like a pretty heavy lift for these folks.Of course you can teach theory but then you have real estate reality..  

It's been extremely underwhelming, not that costly but it's pretty bad. 

You claim it was because we took to long but as I recall the things we were going to do for you were pretty much talked about and scheduled  within the same month of you purchasing the property.