Wasn't really a struggle, at least in Morrowind - you could grab reasonably valuable things from randomly strewn about barrels with and crates random loot in them.
And even easier in Oblivion. After stepping out of the tutorial dungeon, you'd obviously go up the hill to that freakin' huge Imperial City to sell off the junk you picked up that you don't need..... and what's there in the Market District? Dozens of boxes/crates/barrels filled with 0-4gp junk & clothing plus the occasional repair hammer, lockpick, and gold coin.
In fact, I will even go as far to say that sometimes getting special over-powered gear for pre-ordering games has really diminished the enjoyment of the game. I have found myself not installing those pre-game 'reward' bonuses many times because they often break those lower levels that are the most enjoyable.
Yeah, that seemed kind of silly in Fallout: New Vegas. Fallout games are "survival" games - why would you want a bunch of starting bonus items?
(Meanwhile... the Mass Effect 2 bonus armor wasn't terribly powerful.... and was uglier & less useful than the default armor. And the Dragon Age 1 bonus armor was.... useless, since it had a strength req that you couldn't fulfil until you'd gained a bunch of levels. So it was either some starting cash - somewhat overpowered - or a white elephant taking up some of your valuable limited inventory space.)
Yep - don't really bother installing "bonus" starting items anymore.