For example, the pipe character results in the > character and I haven't been able to locate it.

See https://trisquel.info/fr/forum/how-get-keys-thinkpad-t60-german-keyboard-layout#comment-60582

I found opening applications not slow but a little sluggish.

It may be because you are using a Live CD (access to CDs are slow). If you feel the same way after the install, you may want to try Trisquel Mini.

Does the fact the 64-bit live cd is operating that the chipset supports a 64-bit OS?

Yes.

Can someone provide a checklist of tests I should perform through the live cd to see what works and what may not?

Besides graphics (3D acceleration, video decoding acceleration, etc.), everything should work. If you buy a Wifi card, go for the only vendors that guarantee Linux-libre can perfectly drive them: http://libre.thinkpenguin.com or http://tehnoetic.com

root 20 GB, swap 5-6 GB, home 55 GB?

20 GB for / is a lot unless you plan to install several heavy games, you use applications that write a lot to /tmp (Popcorn Time for instance), etc. You can take a look at how much space you use in the root partition of your other systems (and maybe double the number to feel at ease):
$ df -h

5-6 GB for a swap partition is a lot too. When the system swaps (because the main memory is all used), it becomes close to unusable and I doubt you will have the patience to run a desktop system that uses 5-6 GB of swap. That said, if you want to suspend your system (to save energy), then be aware that the whole memory that is used is dumped to the swap partition, which must therefore be sufficiently large.

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