I would advise this: ally with a faction that has a safehouse. Unload everything with weight besides a weapon or two. And a suit of armor. Should you have a good repair skill stock up on stimpacks and sensor modules. And of course ammunition.
Just outside the entrance is a suitcase and a duffel bag. You can use those as a safe place to store gear if you become overencumbered. Which you will. There is vendor and repair in the divide so bring some caps to start.
I would advise these skills.
100 preferred weapon skill, 50 lockpick, science, and 60 or better speach, if you have survival as well that seems like it may benefit as well.
Stock up on stimpacks for certain. And if your repair is good. Bring sensor modules too.
Enjoy the lonesome road. (as of now I have only found one truly safe place to store goods in the divide. A weapons crate next to where you find the detonation gun. Or the armory just a little south if that.)
If you're on hardcoe more and ready to brave the divide. Use super stimpacks instead.