After many hours and almost as many crashes, I've done everything significant in Fallout: New Vegas, and am comfortable with checking it off as completed. By no means does this mean I've finished all the quests or collected all the unique items, but given everything that's in the games I think it's fair to have just finished all the DLCs, seen all of the endings and done most of the sidequests.
I played the DLC out of order, which was a mistake. I played Old World Blues first, followed by Dead Money, Honest Hearts and finished with Lonesome Road. I would have got more out of them storywise if I had played them in release order, but what I really should have done was played them in quality order, building up to the best. I definitely shouldn't have played Dead Money after Old World Blues, as playing the worst DLC after the best can only reflect poorly on the poor one. Reflecting on it, Dead Money probably wasn't as awful as it felt at the time.
Having finished Lonesome Road, I'm not sure why everyone's got a hate-on for it. Alright, it wasn't as epic as the trailer made itself out to be, and it was a touch linear, but it was fun and it was nice to find out some of the Courier's backstory, and the equipment I got out of it was pretty bloody awesome.
Soon I'll be moving onto the Capital Wasteland. I have the Requiem for a Capital Wasteland mod installed so I can go there, and I'll be putting my playtime onto the Steam version of Fallout 3. I'm looking forward to it as Fallout 3 was special to me, but first I need to figure out why my level cap mod isn't working.
Sometime soon I'll put up a list of the mods I have installed, so you can play New Vegas the real way.