I've done a lot of things in my life, and like to consider myself a pretty handy guy, but jesus christ this house is killing me. It's like every time we fix something, something else breaks just to mock us for thinking we could get ahead. So I dremel'd out the grout and replaced the bad spots in the master bath, then I recaulked it with the best caulk money can buy. Then we let it sit for like a week to cure. Then we finally test the water, only to notice the drain is now leaking magically. I then proceeded to spend a very difficult 1/2 hour chistling out lead from the old drain, and pulling out the oakum. And if that wasn't hard enough we decided to replace the drain completely.* So armed with a new drain assembly I decided to remove the old one. Guess what...it's not easy. Took about 6 cutting wheels to get thru the metal (fiberglass reinforced even). After that it was pretty much easy though. Although reaching the nut from the bottom via the hole the downstairs bathroom fan was in was very hard. I think I pulled a muscle..:( behold the joy that was my life for 1/2. Damn near blew out my kness crouching like that for so long:

Mmmmm...yummy. Most of that dust is actually the damn cutting disc's

Shot from below of the old pipe, and drain sleeve freshly cut off (bottom part anyways)

Better shot after I cut off the pipe...god what a cheap piece of crap drain assembly!

Yummy, this is what 10 dollars will get you at the local store :)

Just a dry fit to make sure the cuts are all correct, the pipe has to be perfectly centered in the drain hole pretty much. When working with pvc always dry fit your connections first.

Voila, new drain in place. The nice thing is the new drain uses a compression gasket instead of lead and oakum. Very snazzy.
*see, here's the thing. If we kept the old drain then I'd have to repack the sleeve with oakum and use some type of lead substitute to seal it. And the odds of that working are pretty crappy, especially if the leak is caused by the drain sleeve itself.