I started on very hard (I still have the character). There weren't many areas I had any difficulty with. I found Abernathy Farm early and they served as my trader for awhile. Drumlin Diner was the next trader I found. I stayed around the NW area of the map for as long as possible, discovering every location there and levelling up as soon as possible. I then decided to start the main quest. Found Dogmeat, the Minute Men and then made a B-line to Diamond City in my new found power armour. Made it. Fast travelled back, dropped the power armour off and pretty much left it there to gather dust.
I then started completing my secondary quests and started exploring outwards. In a more circular fashion, starting Southward and moving North East, basically expanding the radius with every trip. Never had any problems with ammo, medical items or junk. I have a tendency to pick up everything that's not bolted down and then fast travel back to Sanctuary drop my junk off, do my trading rounds and then go back to whatever I was doing.
The new food system has made healing so much easier. So after getting to level 47 and barely starting the main quest I'm restarting. Moving to survival mode and going on from there. From what I know, I don't see the game getting much more difficult. The enemies might get a bit more spongy and healing might be a bit more annoying, but apart from the uncontrollable "one shots" I don't see it being harder.
Basically I'm going to prioritise gunnut, rifleman and gun nut. I've seen many people say how luck is OP, but I haven't seen it.