When I get to University in September (anyone in the Boston area, let me know!), I am looking to run the T-A-GDQ path of supermodules. The only difference is that I will be using the HackMaster 4th Edition versions, and will be running it in the world of the Knights of the Dinner Table. I will probably start out using B1 "Quest for the Unknown" as a funnel, and then allow the characters to either proceed to the Little Keep or to the Temple of Existential Evil (a rare module, but somehow I have two copies!). Then they will go through Smackdon the Slavers (sic) and into Annihilate the Giants. After that, I will probably start blending Descent into the Netherdeep with the 3e module "City of the Spider Queen," and Melanee will start to figure prominently in the denouement.
One thing I am having trouble with predicting, however, is pacing. There are at least 50 monster encounters in Little Keep on the Borderland, which means 100 EP's if the Knights hit all of them (which they won't, but given wandering monster encounters and traps, 100 EP's would be a conservative estimate). When they are done with Little Keep, the players should be around Level 3. Slavers has about 80 fixed encounters, meaning another 160 EP's (again, a conservative estimate). Allowing for random bonus EP's, the Knights should be around level 5 when they go into Giants. Most Giants can one-shot a level 5 character, though...
I did something similar in an OD&D game I ran, which ended up converting to 3.5 by the time they made it to T1-4. I was getting annoyed with OD&D's lack of a skills system, and THAC0 also annoyed me. I started with B1 and then ran them through B3 and UK5(or 6? the mountain one), then L1 and L2, before moving on to T1-4. I think they made it to about level 4 or 5 or so before T1.
Oh I forgot, we started A1 but abandoned it and went to T1-4 because I loathed the linearity. I think somebody pointed that out above. The A series is pretty bad. But, frankly, T1-4/GDQ isn't much better.
I think we all have a certain amount of nostalgia for the old modules, but most of them are pretty primitive. I imagine that was probably by design, but at this stage of my life, I'm looking for something that's a little easier / higher quality to run right out of the gate. (In the end, I'll probably just code something from the ground up, of course.)