I have the Dead Money and Honest Hearts DLCs, I have yet to do any of the DLCs for NV.....yet I have over a hundred hours put in. haha

Which do you think would be best to do first?

My character's tags are Guns/Medicine/Speech.

My roleplay is that of a Catholic, ghoul wanderer who finds himself wrapped up in a civil war, helping the wasteland, and recently he has received two messages on his radio.

He sides with House, but will help the NCR when he thinks it is right. So, which order do you guys think would be best? HH then DM or DM then HH?

Well in the order of release, it was dead money then honest hearts. I would probably do honest hearts with your skill set as melee and science (slightly) are helpful in Dead money.

Personally, I like OWB first for all its neat little toys and upgrades, makes the rest a little easier for me anyway. LR is a good early pick as it can be revisited. Dead Money I only ever went to once, in all five playthroughs, it was sorely disappointing but I hope you have fun with it, always saved it for last. HH is quick and painless, revisitable and nice to explore.

I'm asking this from a roleplaying point of view, so I'll try to save LR for last.

Sadly I don't have OWB. =/

Thanks for the advise guys! =)