It's family and I do much of the engineering/cost modeling work for the existing operation.

Have had good luck with german american farmers mutual for acvs and All-State for replacement.

Replacement Cost:  the cost to rebuild the structure with the same kind and quality2.

The cost of living is extremely low compared to other cities and you can still many many positive cash flowing and 1% deals here.

You know him better, so use your intuition to determine the best way to have this conversation.Silly question, and maybe I am just naive, but don't most contractors bake these admin/reimbursement costs into their total quote?

During COVID, evictions stacked up costing tons of legal fees and bad debt.  

I'm not sure what area you are looking at but purchasing a lot here in colorado for example you'll have the costs of drilling a well, installing a septic system, running power to your lot, installing a driveway, etc, etc.

Is there a way I can wrap renovation costs into a conventional loan?

For a property with $101k income, it might be worthwhile upon purchase to do a cost segregation study so that you can front load the depreciation.

Seems like NNN is aSlam Dunk At 6-7 Cap Rates.If you can borrow at similar costs tocap rates and put 30-40% Down.