"However if I purchase the stock again on Dec 8, I technically own the stock on the Date of Record, but I do not qualify for the dividend because the record of ownership for the second purchase is Dec 10th, two days after I purchased the stock."
Yep you got it though I would clarify that you PURCHASED the stock on dec 8th but do not OWN those shares until dec 10th. Your first purchase gets you the dividend. Your second does not. The distinction between purchase and ownership is important for more than just dividends. Voting rights, class action lawsuits are two others that go by ownership.