It's been a lifelong goal of mine to have land to keep as many cars on as I want, to build a homestead, grow food (ie permaculture), etc.

But part of this game is following the Pareto Principle and building in a margin of safety for the big-ticket items. 

But then you need to find food management which may be the more difficult thing to find of the two.I have not had as difficult of a time finding properties as you have described but that is probably because of the market I am in, the people I have partnered with, and the connections I have made over the past 4 years or so.I would suggest finding a mentor, bringing value, and then doing what your shows you to do.Good Luck.

Cleaning out units, I plan to pay a cleaning company for turnover and pass on any extra fees for cleaning out units (like left furniture/food etc.) onto the tenants via a deduction in security deposit. 

The immediate cash flow is more like a safety cushion at this point rather than money I have to have to spend now.

Its a business I run...It puts food on the table for my family.  

I have some experience, having knocked down a drive through location and replaced it with a national food service company in a nice town and then also purchasing a historic bank building and leasing it out as office space. 

No, it was left for City building and safety purposes.

I’m looking at a duplex to fourplex for my first property and just want to make sure I have enough of a safety net before I jump in.

The tenant may decline to provide the name of the perpetrator for safety reasons.