I'm quite late to this thread, but I'll give you my two cents on chucks and hollowing…
I think all the big brands are reasonable, so pick a company and stick with it. I went with Vicmarc, and I'm quite happy with them. As a plus, Grizzly makes a Vicmarc clone that can be used to hold their cole jaws and other accessories… For $109, the Grizzly chuck preforms pretty well, and I bought one just to keep my Vicmarc cole jaws mounted on.
For hollowing, you've got to decide if you want to do the whole thing by hand or use some kind of system. I use the monster articulated system for 90% of my hollowforms, and I'm quite happy with it. JT turnings makes a Gizmo and Kobra makes an articulated system as well… Both of them are beefier than the Monster, but they're also more expensive.
Lots of folks use a D bar type system with great success… I own the Monster version, but I've never used it. Many people make their own. I've used the Carter hollow roller just a little bit, and it's a very nice captured system. With any of the hollowing systems, the size of the bar is the main determinant of the depth and width you can hollow.
For hand held hollowing, their are a number of options. I use my Monster tools in a handle at times, but I generally prefer to use them in the articulated system. I've made a number of homemade hollowing tools with 1/2" cold rolled steel and HSS cutter from Enco… They work fine, and you can't beat the price. There are tutorials on a number of sites with instructions for making your own. The one purchased tool that I use a lot is the Sorby midi swan neck hollower… Even for pieces that I hollow with the Monster rig, I find this little tool is great for smoothing the area under the shoulder of forms with small openings. Lots of folks use the Easy tools, but I've held off on them secondary to the expense of the replacement cutters… The carbide tools are great, but I get choked up thinking about the ongoing costs. Lots of folks with metal working capabilities have made knock offs of the carbide tools, but I haven't made that leap yet.
If you're just starting out, I'd recommend making a few tools in the Ellsworth style from some cold rolled steel and HSS cutters. For less than $50, you can make several of those tools with varying configurations and do a whole lot of small hollow forms. Once you get a feel for how you like to work, you'll be able to make the step to purchased hollowing tools… Just don't be surprised if you find yourself reaching back for those homemade tools every now and then even after you've got one of the hollowing systems.
BTW, I used to buy pen blanks from you on Ebay several years ago… I've still got some very pretty curly Narra blanks that I got from you then. You were always one of my favorite sources for pen blanks!
