I have a jumbo and a timeless tote. I find the jumbo way too hard to get in and out of everyday and the chain strap isn't nearly as comfortable. I love my jumbo but use it for times when I'm not constantly in and out of my bag. My tote gets way more use.
Black Jumbo. its my go to bag which i wear cross body as i have 2 young children. However, it is a single flap and i find it very easy to get in and out of. i rarely use my reissues because of the double flap which i find very annoying
I use my Boys as everyday bags. Also reissues and WOCs. There are a number of seasonal bags in durable fabrics that work well for every day too. It all depends on your personal style and how much you need to carry.
I change my bags often, but for those times when I don't (moving, etc.), it's a 2.55 (reissue) bag hands down. They can take pretty much anything from being put under airline seats to being used daily for months and still look fabulous.