He have literally nothing to offer on early lvls, not even scav vest, his barters are useless (at least on first 2 loyalty lvls) I'm now lvl 28 and still can't purchase kirasa, his prices on mid and high end gear are exorbitant, you can buy pretty much anything he has from flea for half price with same or slightly less durability, on top of that Skier pays more for any kind of clothing or gear Ragman can buy, so whats the point? He has nothing "exclusive" to offer except headsets and balaclavas but lvling him up is straight waste of money since Skier pay more and have a lot more useful gear set on higher lvls.
In my opinion, he should have more simple gear on early lvls to buy with cash instead of inefficient barters, his prices should also go down, shite ceramic lvl 3 and 4 armors for 60k? They are useless after 2 repairs, ulach for 85k? You can buy one with full dura for 50-60k from flea, headsets are usually cheaper on flea as well. Ratnik helmet is literally only thing I would consider to buy of him and now afaik he not even selling gen4.