Find a bikeshop that will let you test ride a bike with Di2 and figure it out for yourself. The shifting is superlative and electronics end up being unobtrusive in daily use. Recharging the battery is infrequent enough to be nearly a non-issue.
"If things go wrong..." is a flimsy argument against, because things rarely go wrong with Di2. However, I will add a data point here -- with first gen, early adopters of DA Di2, there were parts availability issues. Customer crashed and broke a shifter; replacement shift lever assembly took weeks to replace simply because Shimano USA was out of stock, awaiting arrival of shipment from overseas.
First Di2 bike I ever wired, it was like, "WTF am I doing, installing a wiring harness on a bike -- this is so wrong..." I'm a luddite when it comes to electronics, and my personal bike is mechanical shifting.
But I can see where many might prefer electronic shifting systems. To each their own. Potential buyers really should test ride a Di2-equipped bike to see if it's right for them, but one thing said of it is, "If you can't afford it, don't try it out..." because it is good enough that you will want it. Especially in the case of the OP, riding on a group a few generations from current...