What should I be looking to spend on a good sharpener plus brake/spinner?
Bailey's sells a basic chain spinner / breaker set with a chart for $105 (http://www.baileysonline.com/itemdetail.asp?item=SBC&catID=10178); you might find the same on sale or under a different label for a few dollars less. The Oregon versions will cost $170. If you just want something to get started, you might try the Grandberg Break-N-Mend for $45 (http://www.baileysonline.com/itemdetail.asp?item=46605&catID=10175) which a number of A.S. members like. It is a tool that you can keep in your tool box for field use, even if you end up getting a bench mount set later.
You should be able to get an Oregon 511A grinder (or Speed Star equivalent) for under $300. The upgraded 511AX (JollyStar) versions go for about $50 more. The Chinese knock offs start just under $100.
Check out the A.S. vendors listed in the banner ads up on top to see what pricing or sales they have.
Philbert