100%. Scenarios like yours are the exactly the kind of stuff that's hard to predict before hand and can throw you off. 

pillar

Scroogey

bitcoin_beginners

Questions about your cold wallets rotation

DarthCoin

That's a very good point!

I used an old laptop with a read-only Tails stick like a hardware wallet (Electrum, offline, sign-only, xpub exported to the online computer).

What I didn't realize is that the updated Electrum on the online eventually produced unsigned transactions that the offline couldn't understand anymore.

No problem, update the offline. Huh, new Tails doesn't run on 32-bit anymore, and the offline laptop doesn't run 64-bit.

Sure, I solved it after cursing a few hours ("how the fuck can you make PBST incompatible?"). But it got me thinking about myself in 20 years.
Sign a transaction as exercise every couple of months is excellent advice!