1. Finding a holy grail record with no record inside.
Examples of some recordless covers I have found:
Banana Splits; Lenny and The Squigtones; Dick Hyman Moog: The Electric Eclectics of Dick Hyman; Yma Sumac Legend of the Sun Virgin; George Shearing Latin Escapade;  Lancelot Link, The Scramblers (2 different records no less!).
2. Finding a holy grail record with the wrong record inside. Yes, a painful thought but it's part of the treasure hunt.
Esquivel Strings Aflame; Jack Costanzo Mr. Bongo
3. Finding the record but no cover.
Nearly everyone has this record on their holy grail list: Les Baxter Space Escapade. One of the best record covers of all time which someone lost somewhere but at least I found the record!
4. Having someone you know who isn't a record collector find records you want.....for a quarter.
5. Venturing into a record store to find some old guy pulling out stacks of records you want.
6. Having the thrift store clerk tell you "Yesterday we had some guy buy a huge pile of jazz records we had just put out."
7.  Some guy who works at the thrift store notices you collect records and says he has a bunch of old records -- good stuff he says. "Yeah, I got all that stuff, Jimi Hendrix, Janis Joplin, all the good stuff.  So when he brings his records for you to look at, you see every bloody Journey and REO Speedwagon release ever made. plus a few Jethro Tull and Jackson Browne to boot.  Yes, for certain all the good stuff you could ever dream of!
8.  A friend of your parents tells you he just threw out 500 old records his musician father owned. Oh, the horror!
Record Collecting Horrors
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One of the worst situations is for me to encounter an old fart I call Red.  Red has glasses and a really red face and is about 75 years old.  He makes the local thrift store rounds and once in awhile, gets there before me.  He doesn't know it, but he tortures me by looking through each record, staring at it for what seems like eons, examining the front, the back, the inside, the record, then front and back again.  It takes him about an hour to look through about a 2 inch stack of records.  I once waited almost an hour for this elderly gentleman to finish perusing the stack of vinyl on the floor.  And yes, he took all the good stuff and left me with one decent record, Jimi Hendrix Smash Hits. This guy raises my blood pressure.  I cringe when I see him.