Curl, I have both large (quart) jars and smaller (half-pint) jars. I find the smaller jars better for day-to-day use. All (or at least most) of my tins that I open get transferred to a half-pint jar. I always have too many things open at once and it takes me too long to finish a tin. Transferring to a jar ensures that it won't dry out on me.
For bulk tobacco, I usually put a pound into 3 jars. Any left over goes into a half-pint jar (or two) for my normal rotation. When that is empty, I refill from one of my larger jars. When I'm down to my last quart jar, it is time to think about re-ordering.
You could store everything in small jars. I'd probably find it annoying to fill so many jars when I get several pounds of tobacco delivered. I do realize that, in the end, I eventually do this one by one as I re-fill the small jar every couple of weeks. I'm rather impatient (thus defying the myth that pipe smokers are all relaxed and pensive and low key), but, it would certainly work: a large stash of small jars would be just fine.
Grouchydog is probably right that with a bit more effort you could fit more tobacco into a jar and maybe get close to a 1 to 2 ratio. Someone posted a pic a while back where they showed how they used a large (contractor size) caulking gun to compress tobacco into their mason jars. For the few pounds I keep on hand, I'm not so worried about minimizing the number of jars. If you are putting up 100 pounds of bulk, you might need to be more concerned with packing more tobacco into fewer jars.