Switching over to a 465 is not terribly difficult. Aligning the bell housing and adjusting the clutch may cause some headaches but once they are set your good to go.
I prefer to run a 2wd 465 and a divorced transfer case. It makes changing the clutch a whole lot easier and all of the 2wd's had 35 splines eliminating one of the few weak links. As for the transfer case you have the room for a divorced and having a divorced lets you have tons of options later on. The classic 205 has proven itself, is quite cheap, and is mildly upgradable. If your toque increases and your foot gets heavier you can easily step up to one of the more expensive divorced cases from atlas, scs, etc later on.
The best way I have found to make the switch is to head to your local pick and pull and find a truck with a v8 and sm465. A bell housing from a 350 will also mate to many 454's. I am covering my butt in case someone finds one that does not mate but I believe the bolt pattern is the same on all the v8 blocks. There are some BEEFY ones in some of the larger trucks like sidekicks with 454's that have a larger input shaft. While you can put upwards of 600lbs into these the lager input shaft limits your clutch choices. I drive fairy stupid(off road) and have yet to need one of the larger input 465's. The standard input shaft will stand up to a lot of abuse.
As for bell housing choices you have 2. They are either full or half that is not the technical term I know but works to describe them. The full bell housing can be found practically anywhere and almost all of them are aluminum. You can also buy a full one from next to any shop that deals with transmissions. It is really the way to go you will need the 153 tooth flywheel if you want to stick with stock ish parts.
The half bell housing lets you have a larger flywheel and larger clutch and is cast. Although I am sure some out there is making aluminum ones. The downside is that these are getting hard to find. If you see one off ebay or something good chance it is for a 420 not a 465. The piliot diameter ring is smaller on the sm420. It is 4.667" for the SM420 and 5.125" for the SM465 you can have the 420 bell housing machined to open it up. But I have never personally done it before. You also have to adapt a different slave cylinder mounting bracket as the half housing used a manual style linkage. It is a lot of hoops to jump through to get the larger clutch which is only 1/2 to 1" larger then the one used with the full bell housing.
The easiest approach is to find a truck with a 465 at your local pick and pull and pull everything. The bell housing, clutch, flywheel, slave, fork, bearing,(all the old parts inside the bell housing) also get the pedal, linkage, master, and hose. I have taken the aligning pins before out of a junk yard block and actually had them match up to my new block so if you can get them out easily that could not hurt.
Then align the bell housing. Here is just one of the many videos that will help:
Then take all those old parts down to your local parts store(when they are not busy) and get all new parts. Having the old parts will make it tons easier to order new or upgraded ones. If the clutch and flywheel look decent or new you can run them. I know I have before on dedicated trail rigs. But on something that will be used for daily driving it is just best to replace the clutch and resurface the flywheel now while everything is apart.
Oh and while your at the truck before it gets crushed get the vin and year and note if it is anything Wierd like a dually, 350, or bread truck. Not doing this may have you kicking yourself later. It also makes it easier to just say you want a clutch for a 87 Chevy 2500 5.7 then explaining to the kid what kind of clutch numbers you need. Although I would still look into cross referencing clutch numbers to make sure the kid is selling you the correct part insted of finding out back at the house.