Well, there are a few ways I think you could optimize your char, more int would get you faster skill gain, more str for more carry weight. Light step and cannibal id probably drop, you are probably better off putting the points from tough into str to get melee bonuses and some hp rather than all hp bonuses. Chain smoker is an easy point, its not hard to get past for a decent player. Put that point in dodge and its well and truly paid for itself. Hobo can be a very hard start, but its 4 points. 4 points can get you some pretty badass stuff. I can get 12 points in negitives without it being an issue, heavy sleeper and poor hearing are almost good perks for me. And without 10 per IIRC you cannot always see mines, eventually this will kill you.
But in the end you char is up to you.
For the ultimate looter id aim from something better than the shelter, probably a house in town that is more central, near water and a gas station, on the edge of town near a field if you want to build a totally new base.
Id run the looting in a few stages. Stage 1 would be clearing, low encumbrance, decent armor, kill em all and butcher them, whack the sides of houses to check inside for zombies. Clear till your hp is low or till you have gone a block or 2 beyond your looting area to have a safe zone.
Stage 2 would be grabbing all the non perishable food/drinks/stuff you want at your base, rucksacks and shopping carts to be called for imo.
Stage 3 you go through with tools and fire on a destruction/crafting binge. Want to be rocking the drugs hard to keep your focus up.
Id want to carry a high powered handgun like the redhawk for the bits where I had higher torso encumbrance to keep of bears and the like dead.
Eventually id upgrade the trolley to a 2x6 custom loot runner with a large electric motor and plenty of trunks, with a larger customized truck as a basecamp.
Building cars is pretty easy, once you get 2 mechanics, you can use a hacksaw and wrench or just a cbm toolkit to cut stuff off cars, this ups your mechanics skill, so read books to get you to 2 and you are set for mechanics skill.
IME often you can find cars with working wheels and motor outside of town, cars inside seem to lack one or the other. Carry a gallon jug full of fuel to a working car and you sorted for transport for a while. Get a welder and your car and cut up others till you get 6/7 mechanics skill, this is enough to do everything you need for building your own car.
For a good starter looter car id go for the pickup truck, 7 storage spaces right off the bat, make the second seat another storage spot or a bed (‘o’ to remove the seat, the ‘i’ to install bed, seats can be made into beds, you will need a frame to make a box). Drive your car up to within 2 spaces of another car and start hacking useful bits off it. Stuff you cut off wrecks drops to your feet, so do it close to your car, if you try and install heavy stuff while carrying it you will cripple yourself with pain. First you want armor, get some steel plates (roofs and the like) and armor up your front, etc. Extra wheels are a good idea, get the biggest ones you can find, from a big semi trailer, I like to have 8, take some spares as well.
Fuel based cars need refueling, make noise and need to be driven near very explosive things like gas stations, so I go solar. Electric engines seem to be about as powerful as v8s too. Pile the storage batteries in, 6+ is not silly in any way. 2 solar panels is heaps, they break easy, but there are plenty about. Lastly you want lights, rip headlights out of wrecks and maybe some flashing lights from copcars or whatevs.
Installing lights is odd the first time. choose where you want to install your light, then you will be asked to choose a direction for that light. A cursor will spawn on the tile you chose for the light to be in, then you move that cursor to where you want the light to point. So if you put the light on the left side of your car, then move the cursor further left when asked, your light will point directly out the left of your car. Again, not silly at all to have 8 lights on your car. Heaps of lights will help you find your car at night, with 8 storage batteries, you can just always leave them on. They break damn easy so again, take extras.
Fit it out with armored glass, nastier armor, welding kit etc, later, but what I have just described is a totally serviceable basic mobile base.
Drive your Truck for a bit, its good, but unwieldy, you will probably bash into more than a few things and break bits on it, so you want something smaller for a getabout.
2 options: Make something or go for a disposable. Disposable is easiest, look for a vehicle that needs minimal repairs/is already working and grab the jugs of fuel you keep in your truck, fill er up and drive it like you stole it. If it breaks, fix it if its easier then just filling up another car, rinse and repeat.
Custom can be more fun, you want something no wider than 2 spaces and probably no longer than 4, you should be able to zip through wrecks and city streets fairly well in something like this and still have plenty of spaces for trunks. Looks dont matter, a car that is nothing but a seat, huge engine, giant wheels and loot boxes is a damn good car.