Five acres is not something that's going to get developers and investors excited unless you have something unique about the 5 acres, i.e. ocean front.

Her name is Blue Chariot.

It is mostly blue collar. 

Some are now financing out, mostly me providing financing (seller financing).  1 foreclosure, the couple split up.We serve the lower price range, $50k to $80k, blue collar income range, $40k- $60k combined.How to assess risk re the tenant / buyer working out?

If your tenants are blue collar, likely they're using Walmart debit cards, etc.We're experimenting with eRentPayment.com .

I live in Oklahoma so no issues.I have seen wall mounted vent free heaters work as well but you will have to run gas to it. http://www.homedepot.com/p/Dyna-Glo-30-000-BTU-Blue-Flame-Vent-Free-Natural-Gas-Wall-Heater-BF30NMDG/206556618

I'm considering purchasing a 5-plex in Blue Springs, MO (a very nice neighborhood near KC Metro) because the neighborhood and deal look great, but I still have quite a bit of concerns that are preventing me from making the leap.

Their argument is that there is more than enough money in the security deposit to cover the rent and any damages.I can tell them until I'm blue in the face that the security deposit cannot be used as rent. 

As far as areas: doesn't really matter too much to me as long as it's close to a train line so I can get to the Daley Center (clark/lake stop on blue/green/purple, Merchandise mart on brown, lake stop on Red).  

Pass.I just happen to love the ocean and the weather.