Was my upgrade to e-Tap necessary? I think so. Did it make riding more enjoyable? Absolutely. Was the cost burdensome? No, it was trivial.
I was losing the ability to shift using brifters due to a nerve issue, so I mounted TT bar ends and that worked for a while. Once I upgrades to e-Tap, it was like.....heaven, I could shift and shift without unnecessary pain. Would I have upgraded had I not had my problem? Probably not but then again, I would have denied myself an easier shifting and virtually maintenance free derailleur system.
When I could ride upright bikes, were Assos T-Centos bibs worth it? Absolutely, worth 10x their weight in gold.