Well sure you wouldn't likely get something great all that often, but that's part of the game. How often do you find combat armours laying around in random encounters? And you sure as hell are in risk of dying in those. A game mechanic being fair doesn't mean the game should be made easy.
Making ANY game aspect based on waiting is just ridiculous no matter what you say about it. It already gets boring if wait time is counted in minutes or hours but days and weeks? What am I supposed to do in meantime? Steal stuff from Lone wanderer encounters? Remember even if the thieves would be overpowered as hell such as 1 steal = empty inventory no matter what, then you can't do it endlessly. Namecolorizing will make your char useless in less then a weak even if there is 0 reputation drop. Until there is something like disguise and such stealing will be always short term profession. Just look at this topic. People already remember some well known kleptomaniacs. We can defend our property but we are lazy - its more comfortable without the need of looking after our stuff so why not make it that way right?
I think that thieves are way too nerfed when it comes to active playing for the whole season. Even without reputation drops you can pretty much steal only in NCR, you can get always shot and loose everything and you can get marked right away someone sees you with hands aimed towards someone else's back. Some serious boosts AND nerfs should be considered here. As for boosts its mainly reducing reputation drop to reasonable and revertible counts and also possibility not to perform stealing animation from certain skill upwards. Like from 110% and above you would get 0.5% chance not to trigger stealing animation per skillpoint raised. So 110 skill=0% chance not to trigger animation, 150=20% chance to avoid animation, 200=45%, 250=70%, 300=95%.
And as for the nerfs: Steal skill should determine what we can steal and also how much we can steal. So with higher skill we should be able to steal bigger/heavier stuff and in greater amounts. Right now its just check, if you succeed then it does not matter if you are taking 1 or 10 minerals same goes fo 5 or 50 000 caps. So imho 300 skill should be considered as an ultimate point where you can steal anything "regular" with no restrictions in amounts what so ever. And from this point downwards amount and stealing possibilities should decay in reasonable rate. Some of you might say how do you want to steal 50k caps or 2k ammo from inventory but I believe if it can be placed into inventory in such amounts then it can be stolen from there. Also i used word "regular" back there. It because of Pickpocket perk. Right now perk is a must for any decent thief. Without it even desert eagle will be problem for you. But I think our ability to steal such small things like pistols/ammo/caps/drugs and such should depend also on skill and perk would only add possibility to steal bigger and more expensive stuff.
So I think combos could be like this:
Small skill (around 140%) without pickpocket perk = small time robber, easy to get caught if he reaches out for something more than 300 caps or pack of stimpacks.
Small skill with pickpocket perk = more dangerous one, small or mid sized items are not such a problem here but amounts will not get sky high.
High skill (220% and more) without pickpocket perk= can take pretty much anything from 10mm pistol to leather armor or high amounts of caps or ammo. But he will succeed in like 1 out of 2 tries when it comes down to shotguns, rifles, metal and better armors or anything larger (larger and more expensive thing=lesser chance to steal it).
High skill with pickpocket perk = you won't even notice, possibility to steal small or mid sized items with no problems, amount is not an issue here, big and expensive gear stealing chance is somewhere around 2 successful tries out of 3.
300 skill with pickpocket = where is your blue suit?
Also I've suggested that sneaking should affect stealing too so numbers would alter a lot if something like this should be considered but I think you got the idea.