Help me understand what to do next, bicycle shifter woes

I'm not sure what's under the plastic cover. If you can remove the screw and remove the cover, do it. Just don't force anything and break the cover.

I'd leave just the wire cable attached to the lever. Put the housing aside. The shifter works best when there is tension in the cable, which you can supply by pulling the cable.

Spray the heck out of it, then pull the cable and shift up the range, then right back down. Up, up, up, down, down, down. Work the shifter, while pulling the cable. And with lots of lube spray. It shouldn't take very long to figure out if the shifters can be saved.
What do you mean by put the housing aside? At the moment everything is assembled and still attached to the handle bar. Should I remove the shifter from the bar? Or just tilt the bike so the lube doesn't run into the hood?
 
Remove the outer housing next to the shifter, but leave the inner wire attached. You can leave the shifter where it is. The lube will dribble out, but so what? You are going to replace the bar tape anyway, right?
 
Remove the outer housing next to the shifter, but leave the inner wire attached. You can leave the shifter where it is. The lube will dribble out, but so what? You are going to replace the bar tape anyway, right?
Ah, that's what you meant. Yeah I'm going to get some bar tape once I find it. I have a couple of years (tears) in mine. And I have to repair a greavous sin of duct tape. I know about self vulcanizing tape now.

I'm not out of the woods yet but I'm feeling a lot better about this. I'm going to reassemble and see if I can get everything to work.
 
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I've run that series of Ultegra and the Dura-Ace that it was derived from. They are tough shifters. You should never have any reason to disassemble them. If you do, I know a guy who just replaced one of his (broken plastic bit) that I can probably get for parts if you really need it.

There is no reason on any Shimano STI system to EVER disassemble it. That bears repeating.

It either needs cleaning or replacement. Also scrutinize the cable and housing carefully. That's 30 years of experience talking. Very few of these actually fail unless you held both levers and forced them. They don't even break in crashes. Many people are racing on Ultegra, it's the working class racer's kit.
 
Got both sides to work now. Even reasonably set up again. I'll replace the shifter cables tomorrow, just because I bought them. After going through this, I don't think that will be difficult at all.

There's still time for a ride today, so yeah, so that's what I'm doing!
 
Not a long ride at all, just 40 minutes, but enough to get more comfortable with the bike. I know my age and I don't want to push it right off the bat. You have to gradually increase your rides, not go for a century immediately. It sure felt good to have the wind in my face and my legs pumping again. Seems to shift perfectly on the rear derailleur. I need a slight adjustment on the front. I have to nudge it to get it to not rub on the largest front cogwheel.

All in all, I'm pretty happy about a few things.
1) Rode my bike for the first time in two years. That felt good again. I'll go out again in the morning when it's cooler. It's about 85F now. I'll ride a little further, need to work my way back up again, for as long as the season lasts.
2) With everyone's help I was able to get this bike ride-able again. Thanks!
3) I didn't spend $718 at the bike shop to "downgrade" my setup. To be fair, some of that money was to replace worn stuff, but still, that's a lot of cash for an old frame. Think I'll take a little of the savings (ahem, what I didn't spend there) and buy myself an ultrasonic cleaner. I've had numerous occasions to use one, but never bought one. The shifters really could use further cleaning - there's some fine grit in places and I want to get it out of there.
4) I learned a little about these braking shifters. The video I posted, even though it wasn't my model, was both informative and a little bit intense. Not sure I'm quite up to that level of tear down with the limited availability of parts. I wish there were parts breakdowns or at least pictures of parts. Without that, if a spring or something else goes flying you have no idea what to look for, either on the floor, or a catalog, or what to make.
 
I learned long ago if I’m going to mess with something with tiny parts or springs that I haven’t taken apart before, I do the initial teardown inside an open top cardboard box of appropriate size to allow me to work. If something goes flying, it doesn’t go far and/or I hear it hit the cardboard.

I’ll also often cover the bottom with an old terry towel so parts drop and stick where they fall rather than bounce or roll.

I’ve had one to many experiences with tiny or spring loaded parts disappearing into an alternate dimension, never to be seen again…
 
Since the weather is about to become more seasonal, aka significantly colder, I went out for another ride today. Rode about 7 miles, which isn't much, but it was about 50% further than yesterday. Another beautiful day, and a nice ride.

I come back and my wife says, can you take a look at my bike... Umm, yes. Fortunately it looks like a chain fell off the front granny sprocket, and a flat tire. Used a wire hook to grab the chain and get it in position, only took about three tries. My wife had replaced the tire, but it seems the Presta valve is leaking! Was wondering why it was so hard to pump up - it was leaking out nearly as fast as I was pumping it. I had pumped up finally and closed the valve, but I could feel air escaping from the valve. My moistened finger felt cooled by the breeze. Guess I will have to replace the tube tonight. Famous last words, but it shouldn't be too hard. I have the little irons to manipulate the clincher bead. We'll see. Hoping after this work I can test her shifters, she hasn't been on a bike in three years. I'd like to get her riding again, as we first met that way, over 37 years ago.
 
Good to hear your bike is back in running form!

For your next maintenance project: check chain elongation. Note: most people say "chain stretch", but in reality, they don't actually stretch. They elongate because of wear between the pins and rollers, thus making the chain longer.

To check elongation, measure pin to pin distance over 12" length. If you have some 12" calipers, that would be ideal. This video is short and explains the process well...

 
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