I did the paper route money thing up in Mass. and bought from Outer Liimits in Waltham during the mid 80's. I still have most of the prices from the Katy Keene price guide memorized. He was selling Spideys from 21-40 for $4-$7 each and I gradually bought them all. I kept them in the original bags with price tags for over 10 years. In the 90's I was amazed at how little they cost. I also bought a #3 whihc graded at 5.5 for $75 and distinctly remember regretting it after I bought it since it cost so much.
In the late 80's I stopped collecting at issue 300 and the buddy I collected with wanted to buy the Spidey run from me. We figured they were worth $1500 and he offered $900 which I turned down. The run was issue 3, 5-300 standard VG-VF in the early issues and VF-NM in the later issues. So they sat in a box during college and the Army and then ebay and CGC came along and started back up.
The rule for myself was that I wouldn't pay more than $100 for a comic so many key issues and high quality were passed up.
Recently I bought a run of 1940's Walt Disney's from 1-80 for a decent price. He also has 81-200, Uncle Scrooge, Donald, Mickey .... etc. It was a large purchase at a good price for both of us (about 70-80% guide), but now I can't get a hold of him to buy the rest of the issues. Its like I have an empty fishhook and I'm quickly re-baiting. We'll see how that turns out.
Ed