OMG, that's an obscene amount for lot rent.

The drawbacks may be alleviated by delivery services- I know Walmart is offering grocery delivery in more and more areas now, or even the grocery pick-up (where they do your shopping for you when you submit your grocery list and pay for it)- less exposure to slackjaws.
Were I in your shoes, the one thing I would be concerned for in some of the outlying areas is accesibility to emergency services. Fire & ambulance are the main things.

28 years of stuff can build up quick! Have you got help in going through your stuff? Are you selling or donating items? There are several services that will come out an pick up donations.

Man, going through all of our stuff to prepare for another move would be a Sisyphean task.