Two things
When your FTP power number goes up, your TSS goes down for same execution of a workout.
TSS will cycle up and down are you move from recovery back to build etc.
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I also just signed up here and can see that my all my PL is 1.0 and future workouts in my plan really looks too easy compared to what I did prior. I was hoping that TR would analyze my workouts during onboarding and becides setting a eFTP also suggest the progression levels?
Will a Ramp/20min FTP test on TR change this?
No, PL only change up by doing workouts, if “todays” workout looks to easy, use the alternatives to pick on that looks more in line with you abilities, future workouts will get harder as you PL increase
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A fair estimate of your FTP is always a good thing. Initial PL will start at 1.0 regardless. If you feel like the suggested workouts are way to easy, just replace them with a harder alternative. Soon enough you will be challenged, it may take a week or two until PL catches up. Remember that not all workouts should kill you. Two or three intense workouts a week is enough of a challenge, any additional workouts are best spent in z1/z2.
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The cost should be that you are burning more carbs, less fat, so you would have to compensate for that by either taking in more carbs, which can be trained, just like you are training your body to get used to the caffeine. But basically you are likely are less efficient in the sense that for longer races you would like to be able to get more energy from fat instead of carbs as these are more easily depleted.
Since you are using different doses for different length of races, it seems you have that under control, well done.
I did a Gran Fondo last weekend and at some point I could tell I was fatigued and would have needed a little caffeine boost. Well me being stupid I took my phone out to take a pic just to hit another persons back wheel and I got an adrenaline boost from crashing… that brought my attention back in no time and some road rash to remind me to bring some caffeine gels next time. 
And this is only one side of the story, being more alert being one of the benefits but it seems there is more evidence out there that suggests that caffeine indeed also increases performance, I recently read that in a road bike magazine. It will be interesting to see whether more studies can proof that caffeine increases performance or by how much.
If you can find them in the podcast archives, there was a point where Nate was taking huge amounts of caffeine while racing. I’ll bet there was some research talk in those episodes, but it was quite a while back.