And then, whatever the seller was planning to spend, I'd have them pay that amount to me as an cash allowance at closing.

But they would allow you to get an insurable title policy on the property which makes it much easier to sell.

This is one of the problems with housing in lower tier markets because on the surface they appear to be great value but capex makes it impossible in many cases to keep them up and running and therefore the cash flow from your spread sheet rarely translates to reality.

That allows the payment to be low, manageable and easy to cash flow when you transition it into a rental.When you move out you will have more money in the bank, stronger assets, and be cash fluid in case you need to make an offer on more investment properties.

I have a title report from my lawyer, but it is somewhat confusing as the land has been subdivided (it started as 9 acres and is now 1.5) and has quite a few transactions - including to the county (I.e allowing the county to build a road).

Here in Boise, with the upzoning, any SFH, or duplex/triplex/fourplex, you are allowed to build an ADU on. 

I think it was my fault and my ignorance for allowing him to convince me to re-finance properties every 3 years and I think he re-finance 3 of my properties 2 times meaning he earned a $20,000 commission for each property 3 times, or he earned $60,000 for each property just for being my broker.

I will also note that the RC zoning district allows for quite a few extra units so you would get the best use out of your land by building a quadplex or something like that.if you are interested in going forward though I work part time at NOLA builds in town and they do great work for construction at all levels.feel free to reach out if you have more questions 

The cash flow is what allows you to not pay more for your property every month. 

Instead of tying up your capital in a high-cost primary residence, consider taking the would-be down payment and investing it in out-of-state properties.This strategy allows you to diversify your portfolio across multiple assets, spreading risk while potentially generating cash flow and building equity in appreciating markets.