When I put the Roadini together on the cusp of the year by goal was to curabulate (that’s sort of a portmanteau of “curate” and “collaborate”) a road bike that combined the best attributes of all my other road bikes into one genteel age-appropriate package, and I daresay I succeeded:
It’s fantastic, I love everything about it, it’s everything I need in a road bike and more, and when it comes to “sports bikes” I really could stop here and simply ride this one into old age, having only to raise the handlebars one centimeter per year–perfectly doable if I switch to a Nitto Tallux is 225mm long, which would cover me for the next 22 years.
But of course I’m not going to stop there, because like many cyclists I have a problem, which is that I always have to have a project going. So once the Roadini usurped the Milwaukee’s position as Primary All-Around Road Bike, I decided to repurpose the Milwaukee as my racy modern road bike instead. To that end, Ben’s Cycle sent me a Shimano 105 R7000 drivetrain, and here’s where things stood as of last week:

I had resolved to work on the bike slowly and deliberately, but with the weekend coming the temptation to ride it was too great, and so on Friday evening I went at it with a frenzied determination and completed it just as the clock struck midnight:

The bike now feels better than ever, but the biggest improvement to the bike isn’t the new drivetrain; it’s the “new” (actually really old) stem I dug out, which brings the bars a little higher and closer to the Milwaukee’s aging rider. See, at this point in my cycling career I’m not chasing after my handlebars anymore, they’re gonna have to come to me goddamn it! Because I no longer have the flexibility necessary to ride a bike like this:

Then again I don’t think anybody has that kind of flexibility, except maybe for this guy:

That’s a bike that screams, “I can fellate myself.”
As for the Milwaukee, between the recent makeover (actually it was almost two years ago now, but when you’re too old to reach your bars two years ago feels like yesterday) and the new drivetrain it’s looking pretty good for a ten year-old bike. Here it was in 2015 when it was new, also with a 105 drivetrain:

It occurs to me that over the years I’ve had quite a bit of experience with 105:

Or what I prefer to think of as Shimano’s adequacy flagship:

In fact, looking at the timeline…

…it appears I’ve owned and operated every other iteration:

My like affair with 105 started with the second version, which I had on the original Normcore Bike:

The above bicycle is not the original Normcore Bike, which I purchased used in the 1990s and then sold in a stoop sale sometime around the turn of the century; it’s technically the Normcore Bike’s doppelgänger, which I got from Classic Cycle and now serves as my elder son’s commuter:

However this bike is set up, it is nothing less than adequacy incarnate.
I also had the fourth version, in all its 9-speed, Octalink glory, which I used mostly for the cyclocrossing:

Then of course there was the Milwaukee, which came to me with so-called “5700,” which was every bit as adequate as its predecessors with the pointless addition of under-the-bar-tape cable routing:

And now here we are:

While I’ve had a loaner bike with this particular version of 105…

As well as a plastic bike with its virtually indistinguishable Dura-Ace counterpart during my brief return to “racing”…

…this was my first time setting this particular generation up from scratch. It is rather involved, particularly the front derailleur, which requires careful cable routing and tension adjustment. In fact, it’s a lot like putting together Ikea furniture, in that you’ve got to follow the manual carefully, none of it makes any sense while you’re doing it, but as long as you do it right, don’t skip any steps, and don’t think too hard about what you’re doing and why, it all works out in the end. It did work out, too, and the only adjustment I had to make on my maiden voyage was the teeniest little twist of the rear derailleur’s barrel adjuster.
These days I remain partial to semi-custom friction drivetrains, since they work beautifully and are extremely simple and versatile:

Nevertheless, as a former racer I still appreciate the performance and refinement of a modern integrated system, and the new drivetrain delivers all that I could possibly want in that regard:

Though if you do opt for Ultegra and Dura-Ace you get the added excitement of a crank that might explode, a feature which 105 sadly lacks:

But what endears me most to the Milwaukee’s new drivetrain is that it represents the last of its species, as going forward 105 is no longer available with rim brakes, meaning Shimano officially no longer offers rim brakes for any of its road racing groups:

For that, you’ve got to get Tiagra:

Or maybe you can use the new mechanical CUES drop bar levers with rim brakes, I really have no idea:

So in this sense, the Milwaukee in its current form represents the very pinnacle of rim brake adequacy.