They said it was excessive use for 8 years and the water was rushing when they turned it on, so they turned it off to prevent flooding under the house. 

If he sells it to you it would use up a huge percentage of your VA entitlement and prevent you from reaching your goal of financing a multi-family home. 

They are also willing to invest in a bit of preventive maintenance, which helps keep repair costs down.

We also found about $4500 in other items the inspector found (radon, 1 oven not working, a few small leaks, gutters clogged and on minor roof repair, done electrical and plumber work).

This however will not prevent you from selecting a female from all applicants.It may be controversial to discriminate based on gender but in your situation to not do so would be unacceptable to your existing tenants.

You will want to add insulation to prevent the heat loss and stop the condensation.  

Could easily save you thousands and prevent you from into a bad deal that costs you time and money.

I felt like a lot of time and gas had been wasted walking through these properties.I have another idea to prevent wasting time/money, that I think may be better but I'd like some opinions on it...Would it be a bad idea to make offers based off of photos/virtual tours, if said offer gets accepted, use my inspection period to walk through and either go through with it or back out?

I used to wait on the sidewalks till near the end to prevent damage but I hated seeing moms with strollers trying to traverse the busted up old sidewalk or dirt and chunks of rock.

Allowing the soils to drain is the proper fix to prevent the pressure.