What would you do?

I’m thinking of selling my Kelly Elan and instead buying a Chanel Kelly or a classic flap, plus maybe a fun seasonal bag. So 2-3 bags tota. Do you think thay is that a mistake? Will I end up regretting it and wishing I’d kept the Elan?

For reference, I currently own a lavender suede bag, a wallet on chain, and a vanity case. Part of me wonders if I’m just bored. I also get anxious traveling with something that expensive and hard to replace even with insurance based on value.