How far in advance to you plan your Courier's career?
Do you concentrate on story or abilities?
Do you plan the sequence of major events and DLC?

I'm doing one final run before I get caught up in Skyrim (Presumably, that is. Fantasy seems sort of hollow to me now. We'll see).

Here's my plan; I'm wondering if anyone has any good ideas to share. --

Do early exploration around Goodsprings and Primm until level 5 or so. Activate ED-E.
Play first area of Lonesome Road to get Bedroll, Red Glare & unlock commissary.
Sneak up to Vegas to unlock Gun Runners, Clinic and Freeside Casino.
Do Outpost, Novac and Boulder quests; loot Nipton & all west, southwest areas.
Revisit Lonesome Road; play up to end of High Road.
Visit Vegas strip, deal with Benny. Don't visit House, yet.
Old World Blues.
Do all the outlying quests -- Freeside, Casinos, Khans, Boomers, NCR, etc, with general exploration.
Dead Money.
Complete Lonesome Road.
Commit to a faction.
Honest Hearts (It's just more fun at a high level)
Final wanderings.
Endgame.

What's your plan?

I play the way I feel like. On bad days I tend to do bad things, on better days I just stroll around and spend caps. I don't use specific builds nor I plan who I side with in which quest.