engine work and theory crafting

[Unca]

Ok im looking at doing some engine work. atm 454, 850 holly dbl pumper, mechanical secondarys (worked over some...), aluminum intake, hei ignition, tri- y- headers, the cam chains a touch stretched, a few oil leaks and some general annoyance with the looks of things overall... im thinking new cam, rockers, freshen up the rings n bearing, look the heads over do some tweaking if needs be. so. the question....

what cam? think cruiser / toy.. some light to light play.. perhaps dust of a mustang or two... I don't mind a lopy idle but don't want a eternal headache should I decided to take her on a road trip of a couple hundred miles...
chain? or gear drive? .. I like a lil noise but they rob performance.
of course new rings n bearings, new oil pump. gaskets, freeze plugs n such.
upsize the carb some?... I REALLY miss my tune port tbh... carbs are fine but I did enjoy the tpi.
do I do away with the engine fan? go electric fan?
should a guy just go ahead n throw a 496 stroker in it?
forged... just in case..
I know atm I cant hook up the hp / torque ive got but as she grows I think a 4 link n coil overs, Detroit locker.... think heavy footed fun and a desire to smile now n then.
so.. input? thoughts? ideas?
I know budget... ugh. I could freshen her up, throw her back in say for a grand or so. cam n flat tappets.. minimum goodies..
a stroker adds another 1200 or so to it... machine shop$$$$????? im not sure on that one.. anyone have a general idea?

so... lets burn some time on a relaxing sunday evening n help me make a plan n spend some of my tax check...