All great ideas......on the 1956 front, I'm working on that set. You can get nice groups of commons off ebay in lots for reasonable prices and at $300/month, you can finish that set in VGEX to EX uncreased and clean in just a few months--around a year. A Mantle in nice shape might cost you two months, a Robinson a Month, etc. Just depends on what condition you want your cards in. I try to do midgrade at least VGEX to EX clean, uncreased on my Topps sets. There are dozens of most of the 1956 cards online at any given time, so you have a variety to choose from.
I also like Leon's idea of type collecting--with $300 on a given month, you could probably get 8-10 type cards from a variety of sets in VGEX to EX or so from early 1900's to 1940's.
Again, it's all about your tastes. Moving away from new stuff is a great idea. Some of the new stuff is neat but if you collect it, wait a month or two after it's introduced and you can get it for 50% or less what it came out at--at least most of the stuff. Your $300/month will at least retain it's value if you buy vintage cards..........
Good luck!
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