7.3 powerstroke swap to dt444?

Dealing with lots of breakdowns all within last cpl weeks. Grapple truck with dt466e needs swap or in frame, chipper box truck has trans that's going out, and now my stump grinder trailer hauling truck is down.

1999 ford f350 dually with 7.3 powerstroke. "Vin build date Apr 1999" has 328k miles, injectors replaced 120k miles ago. Nice mint body, custom paint etc so I'd like to keep it working, usually used for hauling trailers 10k or little less frequently.
Has crank but no start condition. Called budy with some 7.3 knowledge, he brought laptop over plugged it in and within 15 minutes of cranking, checking, poking around he said: "unable to communicate with the ICM so go buy a new or used one, couple glow plugs are toast so get a set, air box is cracked so seal it up or get a new junkyard cover, also think about swapping injectors and giving it a tune-up" said all this with only using a laptop and looking around for 15min... so ok I know nada bout 7.3 and he seemed to know his ####.

Found a guy with a 2000 f250 with no crank no start condition, he said the icm should be good and his engine issues are internal but it was sitting for over 8months. Well after haggling and for $225 I picked up his ICM "hope it's compatible as I know zip about 7.3", and in the deal cuz he sounded like he knew a bit about the 7.3 I got his complete sinister cold air intake, an in box slightly used k&b closed box cold air intake? And his bully dog guage tuner?

Question is... my engine has 328k miles on original engine, previous owner said he upgraded the trans when it went out around 160,000 miles ago....so all I've done was replaced injectors and routine filter/oil changes. Just bought a large slide in camper which this truck will haul. Planning few local camping weekends in July and a big trip to Arizona and Southern Cali in late aug/sep for family... I need to trust this truck and repairs I choose to make... no problems thus far in the years I've owned it so complained to the same buddy bout my worries to which he replied the following "kinda sternly":
No guarantees even on a new vehicle,
those motors are great little engines with specific care and quality parts used....little gutless but your not in mountains or trying to haul 20k trailers either, your truck is clean and unmolested so just do the icm, full tune up, and injectors as preventative. If your really worried about it before you change the oil send off an oil sample for analysis and see what it says. Oh and don't be stupid and use the chip keep it original...too many engines get F'd up using those dam things... if you insist on doing that crap get a good "TS??" Chip with mild settings and only use it for towing or when you wanna be stupid otherwise leave it off or better yet go ahead and put on the the cold air intake and send in your module for a tune... use the box one these 7.3's seem to like that type better. Didn't argue. Didn't understand half what he said bout the boxed kb cold air intake vs the sinister type... maybe the filter design? And the whole TS chip and send in the module for a tune?

Not looking to role coal but he was right on the gutless aspect.. pulling 10k trailer on small hills in Wisconsin and it def shows its a Clydesdale and not a race horse for sure... so I figure a cold air intake and maybe a chip would help give her just a wee little more umph and speed when towing. BUT DEFINITELY NOT WORTH losing life in it.
Suggestions on doing the cold air intake and what's the difference in the sinister round tube round exposed filter vs the closed box type? Is one superior or give more gains or just safer to use? And the use on a chip... install the bulldog guage tuner "no manual but assume can find online" not even sure if it's a chip/tuner or a program for something else just a small 3inch lcd display with long cord and a print board "assume the chip" that goes inside of the computer? Again no idea if this is a TS chip my buddy was talking bout or what it might contain for programming. So yeah a chip or sending my module in for a tune... I assume module is computer, and then what wait weeks for it to come back... who or where does that? And does it reset itself if it's scanned by a dealership or has work done on tge truck, does it disappear if battery is disconnected... and I gotta do it all over again?

Other option is someone else local said they have newly freshened up dt444 with 105k miles but only a couple hours of run time during testing after rebuild and upgrades out of a bus that they were gonna install into a 1999 ford f350 but decided to build a low rider show truck instead. They said it had cam change, updated internals, head work, upgraded oil pump, oversized injectors etc etc. Setup for mild use and def a tow rig... comes with motor mounts, adapter plate and bell to use with stock transmission and could get from him adapters to change to an Allison trans instead... also said it has installed on the engine already an aftermarket made wire harness and controls along with his 1999 modified computer plug to do a drop in swap with only minor mods to be done with my engine bay. He said my truck has an aftermarket raised hood "it does" which will already allow extra clearance. Anyway he said he's into it for over 12k over the couple years he's been putting it together... way more if you include free work done by his nephew at the machine shop. Nice polite old school fella said he liked the look of my truck with the paint and aftermarket stuff and said he'd like to see his build go into something other than a heap so He offered the entire package to me in a cash&barter propasal. 7k cash as is OR 5k cash and a forklift I have I was pondering on selling at 6k and for that he would put in the motor mounts,move radiator for clearance, drop in the motor and hook it up.
Now the 7k motor alone I wouldn't do, short on cash and don't got the knowhow to do it myself.. but 5k and trade forklift I don't use much and it's installed turn key, mildly built up basicly new upgraded motor has me really thinking... the man has a very nice home and a shop any guy would like... the old signs on his walls are probably worth 20k alone.. retired guy in his early 60's retired as diesel teacher after being in military for 20 years as a mechanic... so I'd say he knows his stuff and if the engine inside is anything like his shop it's been meticulously built.
GREAT DEAL but is it for me? Even the 5k would HURT.
ICM,TUNE UP, SEND OIL SAMPLE AND IF IT COMES BACK OK KEEP IT ON THE ROAD WITH OR WITHOUT INTAKE/TUNE MODS? OR BREAK THE BANK, PISS OFF WIFE PROB, SHORT CHANGE OTHER VEHICLE REPAIRS AND TRUST THE OLD FELLOW WITH A DT444 SWAP?
Honestly if I had the money without the other 2 work vehicles down needing big repairs I wouldn't even second guess it and go for the swap... but is it worth it and what do I have when it's done...big gains with big fuel consumption that's not gonna work for actual working and leisure travel long distance? Or minor gains and cool aspect that will still work as what I need the truck for?