General Outfitting and Questions about Pop-ups vs. Just building something

[Kryptoroxx]

So I'm trying to nail down a list of stuff to pack up for camping and hitting some of these Overland tours that you guys frequently do out here in Socal. After being in the military I am very used to minimal personal gear but on the other hand I always know I won't starve and I won't run out of water. So here's my stab at starting small and including the family in the future. My little one's include one that doesn't walk yet and one that hasn't popped yet so the wife isn't going to be coming along for a little while.

Here's what I have for personal camping gear(not issued):
Rucksack (old Alice, can pack for a week in it)
Sleeping bag system (snugpak winter/desert setup)
Cot, hammock (or I could go with my usual shallow grave)
poncho liner
poncho
sun sail (16.5' triangle) http://www.amazon.com/Coolaroo-Trian...ds=solar+shade (this is a pretty good deal imo)
E-Tool
Knives
Multi-tool
Propane torch
LED hanging light
Headlamp
Hydration bags/Nalgene Bottles
Coolers
Enough 550 cord to make a mummy out of
First Aid Kit (more combat oriented but with some modification it will be more suited for peaceful outings)
Trash bags
Crates/bags to handle food and clothing. Cleanliness is baby wipes and wag bags...oh and an ammo crate to avoid squatting
A few MRE's in case of hell freezing over (yuck!)

What I plan on collecting slowly:
Camo netting pole set (for sun sail drive in/drive out)
Jerry cans for water 2x
Pop-up tent or custom trailer (m101, m353)
3x fuel/water jerry cans
Small Generator
DC fridge or freezer (if it's not in the pop-up)

Specifically for the 4runner:
On Hand:
27" jack (hydro)
spare/roadside tool set
extra fuses
extra oil
fuel jerry can
Tow Straps
Tow Chain

Planned:
Tire Plug Kit
OBA
Extra lighting (4 corner lighting)
Air Bag system
Recovery Points besides stock (sonoran steel has some nice ones for the front)
Rear recovery point insert for tow hitch (till I have a rear bumper)
Fuel Rack
Fold down table
Full Length Top Rack
Gun Safe (for pistol or two)
Winch
Hi-Lift Jack

We (for once) really want to do a pop up trailer but I have zero experience with them and had a few questions. My wife used to travel with her grandparents in one all over the West when she was a kid so that's how I have support from her

1. Is it really even safe to lift them? (not a lot but enough that I wouldn't be worried so much on a forest road)
2. Can I throw extra gear anywhere in them? (like a small generator)
3. Would it be possible to extend the frame say 10" to accommodate jerry cans on the front or back
4. If I pick one up used how expensive are the repair parts (I will probably pick it up used)