Just bought the aforementioned DLCs and I've got 3 different characters at lvl 28, 9, and 4. The highest and lowest are mostly guns and repair characters the latter Im sorta RPing as a cowboy/hunter type guy and I really want to do DM and LR with him. The lvl 8 is an energy weapons/science/explosives type with ultimately bad karma. Thoughts and insight please?

9 is doable, I'm not sure if you'll enjoy seeing how most people hate how 'hard' Dead Money is, but it's definitely doable. I would suggest your highest char. If you really want to play the DLCs with the 4 character, then you should level him/her up more. This is just my 2 cents

I started some where in the 20s. But that was my first time with the DLCs. I may give it a try at lower levels. Some of it was hard even being in the 20s but some of it was easy also. A good balance really.

Take the recommended level suggested in the popup, minus five
I enjoyed LR at level 20, and OWB at level 10. A few challenges here and there (notable bosses and D-Claws) but enemies aren't spongy yet, which is my biggest beef with OWB - enemies either kill you with two hits (Nightstalkers + player has Small Frame) or they have hundreds upon hundreds of hitpoints (Roboscorpions)

Technically the entry levels are more about your weaponry except for Dead Money. Dead Money is doable early on but I prefer to wait until I have a sizable unarmed skill to take advantage of the Bear Trap fist. As I do not otherwise employ Unarmed or Melee, Dead Money comes last. Dead Money is also its own kind of challenge so I appreciate the suspense.

If you're Guns centric I would recommend Honest Hearts first: Survivalist's rifle is probably one of the best unscoped long range weapons in the game aside the .45 auto as one of the best as to accuracy and RoF.

If you prefer energy weapons then OWB: Elijah's jury rigged Tesla cannon and Elijah's LAER are profoundly potent (and fragile).

I tend to play for power and progress a bit on the metagame side but I assure you that OWB is a bit of a challenge but not as much as Dead Money.