JeffB
Legend
I'd just recommend keeping things pretty loose as well in so far as bending the rules go. Just use 4e as a solid mechanical base and then make a game that works for you on top of them, disregarding rules that get in the way or are too fiddly, simplifying them/making them cooler etc in your son's favour. I think this is especially true for magic items.
Absolutely. I myself am not a BTB, love me some rules type of DM. Total opposite. I only skim the surface of rules whatever version of the game we play. My 3.x games were more like C&C in complexity. I would be doing the same thing with 4E. One of the big things is that after experiencing several months of Theater of the Mind style combat in OD&D (the way I have preferred to play/DM since I started with the LBBs in 77), he has absolutely NO, ZERO, ZILCH NADA desire to go back to minis/counters and a grid like we used for PFBB. I tried a 4E game with him a couple months back, and he loved the power cards and different attack options (thus why he mentioned it again recently), but the session crashed and burned. As soon as I pulled out a map, he started rolling his eyes, lol. 30 minutes into the first fight: the "dragon grave dig site" encounter in KOTS (using updated math/monsters, as well as 1/2 hit points for the non-minions) and combat still ongoing, and he was done. Me too. Our long OD&D combats may go 15 minutes. Most are between 5-10.
If I decide to go this route, I would be using Essentials (HOTFL), as I can use the Slayer build therein and pick powers that are not terribly dependent on pushing/pulling/sliding/ and other things that necessitate the grid (or at least necessitate it for my aged brain!). I can reskin some powers to cause conditions that are not involved with nitty gritty movement, etc., but use descriptive terminology. Instead of getting crazy with bursts and blast radii, I can just say " affects 2 closest opponents", or "the Bugbear's mace blow to your breastplate knocks you down to the ground , you will have to get up next round, you won't be able to attack and move" etc. That kind of thing. I can do the same with Monster attacks. The essentials rogue (thief) is where I would have the most difficulty, as many of his powers are move heavy. But if by using the Companion character rules, I could whittle him down to a classic Thief with just some sneaky backstabs , shortbow attacks (current NPC halfling Thief is Blodgett, ) and be the trapmonkey, which is what he excels at in our OD&D game, I am good. Same with a Mage with a handful of fun spells ( in and out of combat) and a stern Cleric of Tyr with some healing, flashy "Tyr's Justice" types of powers and decent melee skills, and I would be very happy.
I am rambling, sorry folks.
Lots of good advice from everyone, thanks, I am taking it all in, and any other suggestions are much appreciated.