Over time I've learned a few things that have helped in my efforts to buy what fits:
1. Don't decant...just fill the jars at the store. This is a great option, if preferred.
But here are a few reasons why I don't use this method: All those large jars would be heavy to transport (a mason jar full just isn't enough for our family of 4 in most cases). Sometimes the tare weight gets overlooked at checkout, which is expensive for glass. (I don't ask for tares, because my containers/bags are very lightweight.) We get rid of all outside "contact" on the jars by decanting...less germs (especially helpful during flu season).
2. Have certain containers/bags that align with certain jars.
My original bulk buying plan was to use the containers offered in the bulk section the first time (like the one shown above with the rubber band around it) + then just wash them out + use them again + again. I've been using those same containers for years + years...and they are the exact right size for decanting into my medium sized Le Parfait jars. I also made a few cloth bags + quickly found which bags partner with which jars in my collection. I know that those bins won't last forever, so I've been practicing using bags more often lately.
3. Have a variety of sizes of jars.
Spaghetti sauce jars, jam jars, bouillon jars, + mason jars offer great variety. Since I cook for a family (instead of just for myself or a couple), I need some larger jars as well. I have a few gallon sized jars for mixing flours + for holding enough granola to last the week. A few different sizes of Le Parfait jars hold family-sized quantities of brown rice, quinoa, oats, dried beans, nuts, etc.
4. Lean toward larger jars.
Perfectly pairing bags with jars is great, but a bag is a flexible thing that can end up a bit overstuffed...so bigger jars leave a little room for a little extra. A not quite full jar is always better than having to use 2 jars in my book...less water used for dishwashing (but 2 jars is a great solution too).
5. It's hard to have too many jars.
And there is always another use for spare jars. ;)
It's totally possible that no one else deals with this problem, since I don't think I've ever heard it mentioned. And yep...this is all just common sense...as are most of my "discoveries". It's mostly just about taking note! :)