Ok, so I have been trying to pay a little more attention when counting down drawers the past few days at work, as I have discovered every coin from before 1960 is worth about $0.50 - 1.00 on eBay.
The only problem being that the profit of selling these coins is eaten up up the cost of a stamp. Unless you sell them in a lot of course. I am going to try someone to sell these coins to locally though and think I can make an extra $15 - 20 a month, barring getting extremely lucky and finding something notably old.
1941 is the oldest I've found so far, a nickel today and the dime from when I started this thread.