My tentative plan for France, Germany, Switzerland and Italy in October.

Your Swiss full fare tickets are only 203 CHF, not enough for a Swiss Travel Pass to be justified unless you want to pay a big premium for the convenience. If your plans are fixed (or will be 60 days ahead) you could buy Saver Day Passes for 52 CHF 60 days ahead for days 7 & 8, that will save a few Francs.

If you are only touring the Black Forest for a day, you can do that with a Baden-Wuerttemberg Ticket, plus the tickets to/from Kehl.

Yes, I love riding carefree on the vaporettos in Venice with the multiday pass.

Too early to buy Trenitalia tickets, you can wait a while for that.

You will love Strasbourg and the villages on the wine route. We didn’t care for Colmar.
I encourage you to spend some more nights on Lake Como. You appear to be rushing through it.
We spent three or four nights in charming Pontresina. We were so very glad we stayed there instead of in St-Moritz.

Ditto to what Suki said above- more time in Lake Como and in Lucerne, I might add.
Have you already purchase the air tickets? Safe travels!

I've already purchased my airfare. I don't want to cut any days off the Alsace part of my trip and this will be my first (maybe only) time in Venice, so I don't really want to cut that short either, which means unfortunately I don't have wiggle room to spend extra time in Lucerne or Lake Como this visit. I'll most likely plan another trip to include Lake Como and hopefully Switzerland as well in the future. The more I've been researching, the more I wish I could travel for months at a time so I didn't have to cut anything short!

From what I've read, the trains between the places I'm going are pretty constant so for the most part I shouldn't have any problem getting from place to place, right? I like to have a general plan, but be open to changes depending on how I'm feeling that day.

Personally, we loved Colmar, so just shows how you need to watch lots of youtube videos and try and judge for yourself as everybody has very differing tastes.

I thought about your suggestions and decided to make a change. Luckily, everything fell into place pretty easily. I'll be spending 2 nights in Lake Como (I've got a lovely room with a balcony overlooking the lake), then moving on to 3 nights in Venice and I cut one night off Florence since I've been there a few times and I'll be in Tuscany again in March. This will allow me a little more time to wander the lake area, while not cutting short my first time in Venice, and will still give me enough time to catch my breath in Florence before heading home (although I'll most likely skip any day trips and just stay in the city).

It's interesting, while on the one hand it's exciting to be able to see lots of different places like I'll be doing on this trip, I also think staying in one place for at least 5 nights is nice and definitely more relaxing.