I was in the same position as milestails, with the difference being I had only played ME1 once on the Xbox, mostly skipping dialogue and just doing the main missions. A couple months back I bought ME1 and M2 DDE for about $5/$10 on Steam, and just a few days ago I decided it was a good time to finally make a serious attempt at the series.
Feels a little weird still not having all the DLC (Pinnacle Station for ME1, regardless of if it's good or not, and the costume packs and other stuff not included with DDE for ME2), but I'll probably get them about the same time I finally decide to get ME3 and go back and fix the very few things I realised I did wrong in ME1 (apparently forgot to intitate a romance somehow, forgot to influence Garrus one more time to get him to say he attempted to rejoin C-Sec in ME2, and a few other minor things). Of course, if ME3 was avaliable on Steam right now I'd go sell everything in my possession and get it right now, but for now I have to wait until I can either be bothered to brave Origin (I have a long history with EA and Origin, and my boycott for their Origin service is still in effect) or they finally send it out to Steam (preferably like Crysis 2 Maximum Edition, where all the DLC is automatically included).
I used the ME2 save editor in the wrong place, so all the ME1 errors I attempted to fix are still present, and I can't stop Conrad Verner going off at me for the gun I never pulled on him or a couple other things ME1 wrongly saves. That's pretty much the only application I have for the save editor, just to ensure all the choices I made are perfect.
Playing ME2 for my first time right now, I'm about 15 hours in (IIRC, I'm on break and I can't be bothered to get my HDD to check Steam). It was very disorientating at first, with how much more focus was put on combat and how a lot of things have changed, but now I'm really getting the hang of it and enjoying it. My aim is still pretty terrible, but nonetheless I still eventually press my way through. Seeing Garrus (I had a lot of chuckling with his mission) and Liara again was fantastic. I've yet to see Wrex and Tali I want to see more of. Ashley was thourghly annoying (Kaiden would have probably been less agressive, but that's for another save). The new party members are pretty cool, although still need to collect Legion, Thane and Samara (probably a few others) and I won't have Kasumi without that DLC.
The story and the jokes are great in both, although, as this is a paragon run, there's not as many as if I did a renegade run (cocky Shepard has a sense of humour). Also, I'm terrible with picking the right team members to get the funny dialogue. Thankfully, there's always YouTube...which I should thank, because it's the reason I'm doing this now. Spent months just watching those less than a minute videos to see some funny dialogue from the ME series. They have influenced me a little bit to try set up conversations to see those things for myself ("Don't piss in my ear and tell me it's raining"), but generally me and my Shepard for the most part do what we do.
One thing, though. I appreciate the removal of the Mako (it wasn't the Mako control that was the problem, it was mainly the hidden objectives and the size of the maps that irritated me), but the scanning mission is probably more annoying for me. Thankfully the wiki has a great load of tips to help. God bless you, nerds everywhere!