Seems to me an element of flexability would be required for this to
work, in addition to the money/piloting skills etc. If you can work
from home from time to time (telecommute), that will help you when the
aircraft goes down for maintainance. Also, what about thunderstorms
during the summer? I would imagine your area of the country can go
through periods of regular thunderstorms late in the day. You are
essentially, I guess, looking for airline reliability from a small
aircraft, which isn't very likely for a number of reasons. However,
with the right flexability at both ends, it might have a chance.

Let us know how it goes !

John