I didn't want to criticise you in any way. Your tips are awesome and well thought out and I just wanted to share my experience with the barter system and add another, maybe useful, way of doing things in Fallout.

It's more a convenience thing than anything else, because I hate the tedious work of picking things up with my main chair, reverse pickpocket them to my companion and do the same thing in reverse for each trade. So I just trade them right away for chems and caps and get rid of the whole weight management for items. I also tend to visit stores and cities more often, so weight doesn't become much of a problem after the first two locations.

Personal preference, I guess.

Oh I didn't take any offense, got a thick skin.

I agree the pack mule method can create some tedious exchanges especially when time comes to sell/trade. Still, it's not exactly the quickest thing either to convert all your money/loot into weightless stimpacks/chems/caps. Both take some doin. That's mainly why I've just stuck with the pack mule method, didn't feel any of the other ways out there really improved on the hassle of it all TOO much.

I'd say frequent trips to cities to sell/whatever is the best way to handle it no matter what strategy you employ though.. Keeps things from pilin up on you.

All the dollar sign does is show what the thing is worth to the other person; if I offer a knife, the notation "$40" tells me that they will give me something worth up to $40 in either goods, bottle caps, or both. In order to get caps via bartering, you *must* find a person who has caps in their inventory and is willing to trade. Any storekeepers in the game have caps on hand for this purpose, and random people on the street have goods and caps they will gladly barter for; in fact, there is at least one merchant, a weapons dealer in Old Town iirc, who constantly replenishes their caps after each transaction, so they never run out.

tl;dr: try bartering with everyone, then bargain for stuff you want, including caps.

The raiders in the camp are a good source of caps if you take all their armor and weapons, get the SMG from vault 15, walk up to one with a desert eagle in a tent and full auto his face, take his DE and start using aimed eye shots and burst fire for anyone who closes the distance. (Abuse line of sight)

Try not to to aggro more than a couple a time. I prefer to do this solo so Ian doesn't get himself killed.

Fighting the bandits early on might not be feasible for OP depending on their stats and such; would be very helpful if they were to post those.

Aaand that right there is why we have money today! =]