Thanks for all the info!! You are all a wealth of knowledge for a newbie like me. One more question....is the Di2 shifters worth the extra money or is it a novelty??? I don't think I can afford them, unless I buy used, but was just curious.

If you want Di2 shifters, you will also need to buy Di2 front derailleur, rear derailleur, battery, battery charger, front junction, rear junction, and wires. They will be about $500 more than mechanical.

That is my decision point #3. :)

My favorite description I read of electronic shifting is that it is like little angles magically putting your chain in exactly the right gear. I want electronic shifting, but I will probably not do the upgrade until next year. Di2 (Shimano) or eTap (SRAM) will not make you faster. But it gives you the ability to shift from both hand positions, and the wiring is a little cleaner than cables. It is also very expensive-- hundreds of dollars more than the mechanical equivalents.

When I do my upgrade, I have not decided which way I will go. I am leaning toward eTap, because I like the easier wiring and individual batteries. I like the eTap shifting approach (left button RD down, right button RD up, both buttons toggle FD). And I totally love the extension blip buttons.

Seems like a solid list. However, now is also a good time to choose a power meter (or not) as well. Mine is a PowerTap C1 chainring (love it) which is only compatible with certain cranksets which would make a big difference in the decision tree.

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Madison photographer Timothy Hughes | Instagram

That is a great point! I will go back and update my list. The power meter totally determines the crankset options. Fortunately, most of crank-based PMs have offerings for both Shimano and SRAM. PowerTap C1, for example, will not work on modern Shimano cranks. And 4iii (a great value option) only supports Shimano. Power2Max does everyone but Shimano.

Just use a Powertap hub. Problem solved.

Unless you have multiple rear wheels like I do. In my case I only have one bike so the chainring meter made sense. If I had two bikes a pedal-based meter would be ideal for me.

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Madison photographer Timothy Hughes | Instagram

So much info!!! Not using a power meter currently, so I won't use one on this build, at least not yet. Being a middle to back of the packer I don't think its advantageous to spend a few hundred dollars on a power meter just to be disappointed with my power output :D
I will be going mechanical on the shifting too. I was just curious as to if it actually added anything. While shifting may be smoother and faster, where I'm at in the pack it ain't going to make a difference. LOL.

One other tactic to consider... depending on your budget and how fast you want to move, consider building it with basic-grade components. These are often very cheap in the used world, and better than you might think. I bought my first tri bike last year, and it came with very basic 105 and other mix components. The 105 stuff was way better than I expected. I will eventually upgrade everything on the bike, but that got me going with a frame I love at the lowest cost (for that frame grade). You could probably build out 105 used for less than half the cost of equivalent Ultegra components.

Agree that 105 will not leave you feeling any lack of quality. 105 today is like Ultegra a few years back, everything trickles down.

Hell, I've still got Sora/Tiagra 9 speed on my road bike and it works perfectly well.

I like this thought process and probably the strategy I will use as I begin buying parts. What about used parts? Should I steer clear of them or is it worth it to get a better used product for the same amount of money as lesser quality new product?

Since a brand new Ultegra 6800 group is so cheap, I would never consider buying anything used.