Yeah after the big cylinder the next purchase would likely be a booster pump so I could use all the air from the big cylinder. Both together used I'm pretty sure I can get for under $1000, while a compressor used seems to be around $3000 plus maybe $500 a year in maintenance costs and air testing fees.It seems to be that the best solution would be to invest in a compressor and just top off tanks as needed and dragging around a bank tank of air seems like a PIA. Also, you aren't going to get full use out of the tank. Once tank's pressure gets down to around the working pressure of the tanks you are trying to fill, you need to drag it back to the shop to refill it. At $50-100 a pop, you could buy a five or ten individual used tanks and just get them all filled at the same time. for the same amount of work.
Re: individual cylinders dive shops seem to quote fill costs on a per cylinder basis, which makes some sense as I am guessing most of the work is in hooking and unhooking them from the system. So filling 5 2l ponies would be dramatically more expensive than filling a single normal 10l tank. But I do need to contact my local fill places and make sure there aren't actually different prices for filling very small or very large tanks.