So, I have both a reissue 226 with RHW and a Navy boy with LGHW. Both purchases were for the intention of daily use! I did get my reissue first and just recently acquired the boy. Out of the two so far, I reach for my reissue so much more. I have the 226 size so it fits a tad more than my boy bag, and I love the understated look of the bag, it doesn't really scream Chanel, unless your a handbag enthusiast Only thing with the reissue, I tend not to wear it when it rains. I know it's been mentioned that the bag is very carefree, but I have a few bags I can wear when it does rain. As for the boy bag, I love this bag too and it's in my rotation. I don't think I wear it as much because the hardware is a shiny LGHW and the capacity is not as good as the reissue. But I love that I can wear it crossbody and it is caviar so really carefree. I know that the reissue can be worn crossbody as well, but for me I find the 226 size just a tad too big to be worn crossbody.
Also to throw into the mix, I have one burgundy jumbo that I have been wearing more than the reissue as of late. I absolutely love my jumbo, but that said, it is a big bag and kind of heavy, so one jumbo is good for me.
I know you also mentioned adding a speedy. I had the same exact thought for myself as well. I had a speedy but sold it because I got all obsessed with Chanel, but now I feel like I should have another canvas piece when I don't want to wear my Chanels.
But after my long winded answer, I think the reissue is a fantastic daily bag!!!