Is shoving pre here ridiculous or +EV? Genuine question. Avoids spots like these and raising off an 18.5BB stack then folding doesn't seem very good. Also, you'd be shoving into a pretty short BB so he has to call off a lot tighter.
As played, would reshove vs the 8 big squeeze definitely. The flat caller can wake up with AA, KK but I think in general he has a hand like he did with the 7s.
That switch can be rough, gl. If I can give you just one piece of advice, or the thing that made the biggest difference for me: Learn how to deal w different stacksizes. The ruleset/ possible lines/ideal play you have for 100bb is vastly different to, let's say, playing w 30bb.