To me, this is an easy answer. A rebuilt 318 is pretty darn reliable. Repaint it, dress it up with the wheels of your choice, maybe add a dual exhaust for the rumble, and enjoy the heck out of it.

408 from Blueprint is a pretty nice little combo for a cruiser, way cheaper than than some new, over complicated fuel injected late model hemi & would make just as much power.

https://blueprintengines.com/produc...small-block-chrysler-longblock-bpc4082ct

Long distance cruiser I'd go with a nice 340/360/408 and some sort of OD trans. Could even stroke the 318 with a 340 stroker crank and put some better heads on it too.

If you go with a 360 get a 5.9 Magnum engine block as they use a roller camshaft. Might as well take advantage of that if starting from scratch.

X2

pretty nice price as well, considering it's dyno'ed and comes with the paperwork.
375hp from that package would put a lot of 440's to shame.

I agree with this answer. The simple and cheapest answer is to add a four barrel intake and carburetor if doesn't already have one. Some headers (worse case) and dual exhaust with lower gears if desired. If he has to have a 440 then look for a running motorhome engine swap on intake, HP Manifolds or headers, and be done. I would suggest a camshaft swap but, with I've seen lately he'll be taking a risk with an improperly machined camshaft itself or defective lifters. The other contender would be if he wanted to build the 440 is having a reputable machine shop or engine builder and accounting for any potential part delays.

K. I. S .S.
A computer that never existed can't strand you miles from home.
Given a choice alongside a roadside if I had to replace a fuel pump 2 bolts on the side of the block beats dropping a tank
.adding in a computer and a gazillion sensors to a car that never had them is asking for trouble.
I've seen some pretty ratty wiring jobs.

Just a FEW examples I have many more. Many of t ehigh $$ cars i have seen fall way short in the wiring dept.
These examples made it all the way across the auction block to the new owners driveway. The 57 was a 200K build in 2008 with a BRAND NEW complete Corvette driveline straight from Chevrolet. Gorgeous build but they couldn't keep the electrical issues under control.

A few AFTER examples

i see you have seen and evicted many of the same "gremlins" i have dealt with over the years.

Yes, it is a common area that is poorly done by most as they have no training in the area and most of the DIY kits Like PAINFUL do not address things like USING THE PROPER CRIMPERS and TERMINALS.
HMM Problem: I don't have the correct sized terminal SOLUTION: Strip extra insulation and fold wire multiple times as needed
OR,
Wire(s) are to big for terminal SOLUTION: Cut as many strands as needed until it fits. THE PRO's know to cut the same number of strands off each wire when shoving multiple wires in to a TOO small terminal LMAO

When did you guys get under the dash of my car and take the "before" pictures?