To be Honest, I prefer that they strip our equipment away at the start of the DLC. My reasoning for this is that it forces you to search the areas for food, aid, ammo, and other items. But most importantly, it forces you to use the DLC's weapons and it helps you get used to them. And it also allows you to bring back more stuff since all your gear stripped at the the beginning of the add-on. That's what I would like, BUT MCA has already said Lonesome Road won't strip away your gear at the beginning of the DLC, so yeah....
If
you really want to do the stuff you said above, why not just leave
all your stuff then?!

IIRC alot of people only took a pistol, some light armour and a few stimpaks to OWB and ended up restarting the DLC. Oh and they complained it was difficult. If other people really wanted to use the DLC items then they would. :yes:
I want the Lonesome Road to be difficult and I hope it is, that's probably why they let us take what ever we want; like OWB. Although, I don't want them to just be like Lobotosponges with their helluv-annoying Brush Guns and their super heightened ESP! :banghead:
I for one will not be taking everything, but I'll take what I think I'll need, a mixture of my stuff and the DLC's stuff. Like OWB, they probably want you to use what you have, because they knew it'd be hard.
Plus I won't be playing Lonesome Road until a week later; when Gun Runner's Arsenal is out!