Hardest and Easiest Games to Win

[Superballer]

Easiest for me would have to be Cliff Hangers; just go $20-$30-$40, with minor adjustments as needed, and you'll pretty much win every time 

Of the current rotation, hardest would be That's Too Much; basically you're shooting in the dark with no help 

[SamJ93]

TTM is hard on the surface, no question,but it's a lot easier if one observes the "one after the big gap" trick. Most of the increases in the prices are around $1000, but there is always one that's a larger jump of around $2000--this is when they're trying to trick you into stopping. Simply go one more price higher than that one, and you'll win a lot of the time.

(Of course, sometimes the correct answer is the price before the gap, in which case, tough cookies--but the "after" scenario occurs just as often from what I can tell.)

[WOF85]

I would put Hi-Lo and Check Out on the hard side.  Like Lucky $even they can be really easy or downright mean with their prices.