Actually, if you do it right, you gain ~40 skill points at early levels; probably zero skill difference in the end mind you, but things are much easier earlier on (and get some perks earlier too).

As for Benny problem......just stay away if you are nervous about it.

For me, it is all about the thrill with minimum equipment and supplies.

Oh I did forget one thing.

4-6000 easy caps from snowglobes.

that DOES make a difference.

But showing the age-old addage you have to have money to make money you have to have money you have to get yourself in the strip.

Everyone play's how they like to play and that's all there is to it, really, but I must comment on the concept of equipment and money, since you're using as an example why not rushing is better.

If I 'sneak' towards Vegas at lvl one, I usually arrive there in 2 hours (takes a while because I'm collecting/selling too) with 2 free combat armors, usually at least one cowboy repeater, a couple 10mm pistols, one sniper rifle (maybe two if I'm feeling lucky), usually enough stuff to make a few repair kits, a fair bit of 9mm, 10mm and 357 ammo, a couple skill books, and 3k caps (varies) from selling all the extra guns, armor, etc that drops/I loot from fighting NPC's & containers as I sneak along. If I actually entered the Strip & started that sequence, I'd have 7000+ caps or more. If I actually fought a few guys (making myself be lvl2 when I near Freeside) it's even more. Obviously, actually picking all this stuff up is completely optional, and would just as obviously make the starting towns very easy if you go back with it all.

The point being, if you already know the game, it isn't time that makes you (relatively) wealthy/well equipped for your level, it's already knowing where things are, and where the 'safe'/easy to get things are.

It's true that the merchant scaling slows you down equipment wise, but not by a lot in terms of being able to handle stuff quite a bit higher than your lvl 1 or 2 chr. You've started/broken no quests, everyone is neutral, and you can decide what you wish to do from there. Whether you enjoy doing it in this fashion is another matter entirely, and of course is completely subjective.

I went north to the strip quick on my Energy run...
Why? more to do with energy items/weapons up there.

I wonder what the lowest level is you can enter the Hoover Dam battle.
You can do a lot of the main storyline without ever killing anyone, as long as factions don't want you dead.
I'm gonna try this.

Haha hell no!

I went (RAN) by the cazadores, that burnt out town w/ raiders, past the fire geckos, then take a right when you see dear ol' cooke cooke. Don't forget to shoot that rapists cow.