A couple items I noticed was the closing costs of $20,000 and the property management.  

I'm also crunching down on my expenses/maintenance items.

Instead landlords are asking that they show proof for  applying for PPP loans, do rent deferment broken out over 12 to 24 months, and then extend the primary lease term 2 to 3 years more for helping cash flow security stream of the center.There are a lot of other items in the lease you can try to re-negotiate with the work out.

They've stated all furnishings, bedding, electronics and daily use items must be removed and relocated into one of the habitable areas.

Definitely take care of some of those financial planning items you mentioned while you have the time.

Year One (Save >15K)Get back home around August; go back to work two weeks later.Sell the truck and trailer.Start prepping the house for renters.Get a job at Wright-Patterson AFB.Sell all unnecessary furniture and miscellaneous.Vet and sign renters.Move to Dayton, store all the necessary furniture, and rent out a motel at monthly rates.

How do I structure a fair and decent term/s for items like roof and HVAC?

But I would keep records related to a property especially on renovations and items like that. 

An LLC is a pass-through entity meaning it pays no tax at the entity level and all items of income and expenses are picked up on the owners' returns.  

Also, he will likely be going around shopping for furniture, kitchenware and other household items after arriving.