What ctubbs said.
If you think you not going to like sharpening, then understand that it will just be that much more difficult with the carbide chisels. And yes, you will need to sharpen them. Putting it off will only give you less practice. Carbide tools get dull also, but they are just harder to sharpen. Also, when most people around here talk about carbide tools, they are talking about the insert type, like the Woodchuck Pen Pro. If you save your money and buy the Pen Pro instead of the PSI set, you'll be very happy. If you buy the PSI set, you'll only regret it when you purchase your Pen Pro. Furthermore, IF you decide this isn't for you, when the time comes to sell, you'll do better with the Pen Pro as I doubt you'd get many takers for the PSI set.
I got impatient, and bought the EWT Mini-finisher, instead of ordering the Pen Pro. The EWT has a thinner shank than the Pen Pro, and that translates to less vibration, and easier turning IMHO.
If your going to do pens, then you'll have to drill holes. That will require either the lathe for drilling, or a drill press.
You can buy 10 pen kits from Smitty for $26.
Buy a mandrel from any vendors who sell them (get the adjustable one). AS, PSI, WoodnWhimsies, Woodturngz, CAUSA, etc... All have them. $16.79.
Look at all the vendors from this site. You can buy 10 pen kits from WnW for $17. That's just an example.
For tools, I agree to not go with "Pen making" tools. I find that a smaller takes more skill than a larger one. At PSI, you can buy a 3/4" roughing gouge for $18.95, and a parting tool for $9.95. You can also get a 3/4" oval skew for $14.95 (1"-1 1/4" are better if you can find them for a decent price). Another $11.95, and you can get a 3/8" spindle gouge (comes in handy). Many people here use the Woodchuck exclusively for pens.
You also won't need a diamond hone to sharpen those HSS Tools. I can tell you from experience that a belt sander won't sharpen a Harbor Freight carbide tool, but I do know that they get dull. Really, some even use a skew from start to finish on pens. I've done it, and it isn't so bad as long as the tool is sharp. Skews are also easy to freehand sharpen because of their large bevel.
I wouldn't use shellwax. My first pen had a finish using CA, and EEE Ultra-Shine. It actually looked pretty good considering I didn't know what I was doing. I found a tutorial on how to apply the CA using the EEE. IF your hesitant to start with a CA finish, you can get Myland's Friction Polish, and Sanding Sealer in 1oz. bottles (that's more than enough) for less than $3/ea at Wood N Whimsies (there's probably other vendors who do so also).
I never used a pen press for my shop. I have a woodworkers vice I bought at HF, and used it with leather(for protecting the pen plating) for assembly. You can also make a Pen Press easily if your of a mind to. Heck, if you have to you can even use one of those pistol grip clamps you see around (I sometime do when I'm putting a pen together at home). Here's the vice I used:
6" Portable Carpenter's Vise
I learned what it felt like when the pen had reached the point where I'd pressed enough with this vise, now I use it at home since my friend has a pen press.
Lets see:
10 pen component sets: $17.00
Roughing gouge: $18.95
Skew $14.95
Parting Tool $9.95
Spindle gouge $11.95
Mandrel $16.79
Friction polish/sanding
sealer
$6.00
Total $80.08
Another $20 for you barrel trimming set brings it to $108.08.
That's about the same you were looking at (maybe even less) before.