Hi there.
I also have a '65 Barracuda. I've gone to full disc brakes on my car. There are many ways to do this. You could gather used stock / Kelsey-Hayes parts and do a retro conversion. There are many posts here and elsewhere on how to do this. I went with the Scarebird (
www.scarebird.com) front disc conversion and I'm super happy with it. Since you're familiar with GM parts, then the Scarebird option will be easy for you because it uses stock GM calipers. For rears I went to SSBC, but this required a huge amount of conversion - new rear end, new custom axles, custom brake lines, etc. While Your In There, do yourself a favor and replace the single chamber master brake cylinder with a proper dual chamber front/rear unit. I wrote up a post a few years ago how to do this. I'll dig up the URL. If you decide to stick with rear drums, then upgrade them to at least 10" drums. The 9" drums are worthless.
As for the engine swap, you can certainly learn a huge amount here, moparts.com, bigblockdart,com, etc. But I'll give you my experience. The most important thing to know is what your goals are. When I replaced my 273 with a 360, I was told by many that the 360 would just drop in. While the 273/318/340/360 blocks are all LA blocks and very similar physically, there are important changes. I found, and continue to find, that users on Internet forums love to tell you as fact that certain things will just work when experience doesn't bare that to be true.
If you swap from the 273, you'll need to change out your bellhousing, clutch, flywheel (the 360 in externally balanced, the 273 is internally balanced), clutch fork (and pivot), driveline, oil pan, heads, intake, engine mounts (from Schumacher), and then you'll probably be stuck with a low-flow 273 exhaust on a 360 unless you spend another $900 on specialty headers that may or may not fit due to the constricted size of the engine bay. Only TTI or Doug's Headers are likely to fit the bill. I also found that 340/360 is not properly cooled from the stock radiator. So given that the 360 also uses a different water pump on the front of the engine where the input and output are switched from the left and right side of the engine, then you'll also need to either have your stock radiator modified to change the ports and have an additional core added, or find, modify, and install a newer radiator. You'll have fewer issues by going to a 318, but much of the above still applies.
I switched my 273 out after it blew one dark and stormy night because I had been led to believe that because the LA 273 was only made for a couple of years, that rebuilding it would be prohibitively expensive. But I guarantee you that it would far cheaper to have a nice 273 build done up by a reputable shop with plenty of modern adaptations than go through modifying everything else.
Simpler still, if your 273 is running well now than simply leave it be. As I said, it all depends on your goals. The 273 is a great motor, but doesn't get the respect it deserves from many circles.
As for other mods, what are you looking for? Engine mods? Drivability mods? Safety mods? MSD ignition/coil is nice. Better heads, intake, perhaps an Edelbrock 500 for your 273. What do you foresee?
-marcus