I personally have found larger tanks are easier to set up and maintain. The initial investment is often more, but if you can do it, do it. I've kept fish my entire life pretty much but up until oct of 09 all I had was a 20g. I got a 55, then 120 and have had 65s,75s,90s,125s135s, 150, 180, 240 and my new setup is a 6x3 300. Each step up led to another learning experience. My 55 had an ac70. The 120 had 2 xp4s. I had moved up to 2 fx5s w the 180. Then came a sump w my 240. Now w my 300 I'm learning different overflow methods and how to build a DIY sump.
Obviously that's quite a number of tanks in less than 2 yes and I think I find the set up and tear down and mechanics of tanks even more fun thank keeping fish.
As far as maintenance cost goes, water is included in my rent and I have my 240 and a 75g growout and my electric bill has yet to exceed 150 yr round.