Most days I'm  just driving around checking on our construction crews, dealing with tenants, or riding around maintaining properties that I don't directly own.

Smokers are not a protected class.If you care about maintaining good landlord-tenant relationships and maintaing your property, you are likely to attract the type of tenant you desire.

I am in an area without large cities, so it's challenging to maintain a list of active investor buyers because there aren't many.  

Of course those areas did not have the concentrated commercial/retail growth around them. 

In addition, in many states, it is ILLEGAL to require the tenant to maintain the property.

If I were you, I'd concentrate on your personal well-being instead of trying to offload a problem (that may not be offloadable) to someone else.This is pretty bad...  

It's really a road, but the county doesn't own or maintain it.  

I feel that way about HOAs in general, except maybe in a condo situation where you're essentially paying them to maintain the exterior of the building and in some cases plumbing is covered by HOA.

There are a couple of different NOLO books, and off the top of my head one was formation and another covered maintaining.

To establish and maintain a good landlord-tenant relationship, start with respectful, open and honest communication.