Ah but you should be somewhat "worried" about the bounces - not worried as in nervous, but they should factor in. You are right they will happen, but the skipping allows him to go much higher than he would with something like a token dose. So he kind of gets trapped in this cycle of shoot to the moon, slam to earth, skip insulin, shoot to the moon, repeat (I don't mean this as harsh, I've been there! Just trying to give analogy/explanation). Giving some insulin will help cut through those bounces a bit, provided it's safe and you can monitor and intervene if needed. I'm guilty of leaving a can of MC/HC out so I can get some freakin sleep
The short answer is we don't know how he'll handle a shot on a bounce break late nadir because it hasn't been done yet (I perused spreadsheet and couldn't find a good recent example). His usual nadir is +4 to +6 ish.
If he were my cat, following SLGS? When I got the 75, I'd have stalled up to an hour to see if he came up to 90, and given a BCS of something like 1/2-2/3 dose if he did come up. If he didn't, I'd have done a very small token dose of 10-25% in the hopes of cutting a bounce a bit (yes I realize this goes against the SLGS rules as written). Just something to help drain the depot a little bit but also help tamper the inevitable bounce.
Today, I'd have shot probably a 1/2 dose BCS when I got the 102, or a token dose if that's more comfortable. Remember food takes at least half hour to kick in.
Also remember, on TR youd be "letting" him get down to 30s before a reduction so the numbers you're seeing are still ok!