In the past, I just used a save game near the end of the game using a high level character and did the DLCs in the order they came out.
I just started a new game (#4) and I was wondering when and in what order to do the DLCs so as not to be overwhelmed but to have enough XP to be able to complete them (since you cannot return unless you do)
I am level 10 and just completed "Come Fly with Me" Should I wait until I am level 20? Also, what skills should I focus on enhancing for each?
Thanks for your input

Dead Money-Wait to be high-leveled, focus on guns
Honest Hearts-No need to be high-leveled, but the "Heartless" perk from OWB helps a lot with the cazadores if you're low-leveled, probably guns again
OWB-Same as HH, except Heartless is less of a problem unless you hang around the East part of the map, Energy Weapons.

me i used to do them the order they came out, i found that around 15 do HH before u talk to mr house, then do DM at around 25+ and then owb whenever. but a heads up, doing them at low levels specially like HH u lose out on cash from the guns cuz at lower lvls there using 9mm/10mm subs and Joshua dont have as much cash on him to sell stuff to, usually around lvl 30 hes got about 3 to 7k cash while at lvl 15 hes got about 600.

This is the order I done them on my recent playthrough...
HH - 15, useful skills - Guns, Sneak
OWB - 22, skills - Energy weapons, Sneak
DM - 28, skills - Energy weapons, Unarmed, Sneak, ( Lockpick, Speech, Science - these are not needed, but very handy to have at 100, 85, and 100 respectfully )

I pretty much done them one after the other, doing only 1-2 quests, if any in between. Skills are dependent on playstyle, but I listed ones that I thought to be most useful.