So this is what the answer eventually was.
I'm not sure what was going on with Random, but it wouldn't select (10,1) in the array. Also, other variations of this code let the button just continue to either pick more letters, pick more letters and then stop or just crash. Choose seems to nip that in the bud and should carry on because 1-10 are the same X coordinates in the array with me moving it down the Y axis +1.
Thank you very much again for the help. Now I've just got to make it take me to a level!
*EDIT* I believe you were also correct about the Else being in the wrong spot. It's a small detail to miss and so I missed it completely. lol (Also coding the way you understand it sticking with it because it works makes sense to me too.)
*EDIT2* I also realized that I needed to change the =/= 0 to = 0 when checking my array (line 25) because when it is 0, it needed to keep going. Because: 0 = bad. It took some time to work the kinks out, but this is the process. I'm just glad there are people that can help.