In the short term, though, you bet I'll be swinging hammers.

However, if you are not personally guaranteeing the mortgage, you bet there are benefits! 

I bet that was an easy sell huh?  

Rent/sale option I would bet the seller knows it.

My bet is no.Your screening process is not just the application of family referrals, bank accounts and the jobs they had yesterday.

@Jennifer H.A middle of the road tactic we frequently employ with our student tenants, if they drop the ball at the beginning of our relationship, is to strictly enforce the late fee - even on the first offence - but, once the late fee is paid, we tell the tenant if there are no further issues throughout the remainder of the lease we will either apply the late fee to their rent at renewal or refund it along with their security deposit.This keeps the relationship with those who honestly made a mistake and, for those who make such conduct a habit, it is - to borrow from @Jeff Rabinowitz - a drop in the liquid fund ;-)

What is the best way to structure the deal so the seller has to take responsibility for remediation and most of the cost to get it back to a basic habitable property?  

Other than that, I tell tenants to not expect the basement to be any better than a garage when it comes to habitability.  

Make a habit of resolving problems as they pop up.  

I bet you do great if you are concerned enough to be asking these questions!