Plus, they likely enjoy helping others and being surrounded by like minded people.

By joining the local REI groups you will be able to surround with like-minded investors, wholesalers, attorneys and other RE professionals. 

Your best option is to do a boat load of market research to demonstrate that the health of the surrounding neighborhoods and community is still strong.

Hayward is still affordable compared to surrounding cities but offers the same features. 

We feel confident that once we apply our own screening criteria, we could find decent section 8 tenants, however, I am questioning, as a safe guard, if it's legal to give a tenant a notice of terminating a lease if the tenant has caused enough damage or incurred enough fees to deplete their security deposit.For a prior experience example, our last Section 8 tenant (the "final straw" tenant) had a $650 security deposit and at one point, had the front door kicked in, breaking  the door, both locks, and breaking the surrounding plaster (not due to a home invasion).

The back is surrounded with woods and other houses on a different street.

Delaware is a small enough state that I actually started calling places in surrounding Maryland/Pennsylvania/New Jersey because everything is so close on the state borders.

I’m from a small town surrounded by about 4-5 other small towns, and I try to stay in that area.

He might know some resources in Chicago or surrounding areas. 

Right now people are desperate for even moderately affordable props in Seattle and surrounding areas, so you're in a good position as the seller.Good luck!