Ok, I've got problem #1 fixed... new o-rings and some lube worked
great.

The second problem is a little more complicated than I originally
thought. The teflon tape did nothing so I got down closer and it does
look like the place where the drain plug screws into the filter is
cracked. The problem is I can't seem to get the stupid sand filter
empty enough to stop the leaking to be able to patch it or do anything
with it. I've had the pumps off for 48 hours and it's still dripping.
It appears to be a metal garden hose sized female plug with a plastic
insert that is attached to it. The sand filter is a 525 lb filter and
it's pretty old. I guess in theory these things should last forever.
Any advice on how to repair the drain cracking?