I bought a cabin about 1 year ago. The past 6 months the well water has been
very muddy red color. This is not constant but is getting more and more
frequent. I talked to surround neighbors, (same side of the mountain) and
they said this happens around here - just put a whole house filter on and
live with it. I on two in line filters on and with in about a 3 week time
span both need replaced. Should I consider calling a well driller and insist
on drilling my well deeper? I talked to one driller and he said if you got
good water flow don't screw with it, you could wind up with no water!

Sounds like iron in the water....

Have it tested, there are number of iron form: bacteria, compounds,
etc.

But first step is to take it to the lab for testing.

number of solutions available, such as chemical treatments that injects
chlorine or ones that use some catalitic reaction on filter, and then
wash away iron with system backwash cycle.

see:
http://www.reopure.com/terminator.html

Anyway do your own research.