I would like to know what all qualifies as completely clean here- Electrical wiring is normal and no unlicensed modifications - Structural inspection is also clean.Seller is ready to discount the price by ~20% from market plus the cost to repaint the whole house What are other questions to ask and things to consider in this scenario?

Maybe I’m reading this wrong but after reading several articles it’s my understanding that normally when a civilian assumes a VA mortgage the “VA entitlement” will remain with the seller meaning purchasing power in the future will be less since it’s still tied into the current loan and the 1 year occupancy is foregone since the seller has lived in it over a year. 

The 2nd question is should we pursue the investment property even though we are more cash strapped than normal due to the remodel and if so, would using a HELOC make sense? 

For a truly depreciating asset like a car or truck or plane it makes sense.

I first got in contact with my GC 20 years ago when he came to plow my driveway as a favor to my normal plow guy.

I have towed many cars off my properties and had to keep tow drivers safe while they do their service.There has been a nice lull for a bit.

Gemini AI can help:Key features of an Ohio Land Contract:Installment Payments: The buyer agrees to purchase the property through regular payments over time, rather than a full upfront payment.Seller Holds Title: The seller retains legal ownership of the property until the full purchase price is paid.Agreement Length: The contract typically extends beyond one year.Property in Ohio: The land in question must be located in the state of Ohio.Improved Property (usually): Land contracts in Ohio normally involve property with a dwelling on it (a house).Here are some additional points to consider:Recorded Contract: A valid land contract must be recorded with the appropriate county recorder's office.Contract Content: The contract should include specific details like the names of the parties, property description, purchase price, payment terms, and down payment amount. 

I would think 10% is lower than normal, but could be wrong.

Normally I attempt to structure the transactions utilizing an interest only 3-5 year ballon payment (balance due in full). 

Hopefully, you have a clause in your lease that states the tenant must return the property back to you in the same or better condition as they received it.You may be able to use this clause to warn the tenant to smoke outside or face damage charges as smoke damage is not normal wear & tear.