Update 2: For the record, this is the finished program incorporating the advice from Mr.Wizard and kguler

DynamicModule[{x, t, status, h}, x[_] = 0; t[_] = 0; status[_] = False; h[_] = {}; Column[{Grid[ MapIndexed[{ #, Button["Start", Speak@#; status[#2] = True; t[#2] = Hold@AbsoluteTime[] -AbsoluteTime[], Enabled -> Dynamic[! status[#2]]], Button[Style["\[Checkmark]", Darker@Green], t[#2] = ReleaseHold[t[#2]]; x[#2]++; AppendTo[h[#2], t[#2]]; status[#2] = False, Enabled -> Dynamic[status[#2]]], Button[Style["\[Times]", Red], t[#2] = ReleaseHold[t[#2]]; x[#2]--; AppendTo[h[#2], -t[#2]]; status[#2] = False, Enabled -> Dynamic[status[#2]]], Button["spell", Speak@StringJoin[Riffle[Characters[#], ","]]], Dynamic[x[#2]], Dynamic[Clock[]; ReleaseHold[NumberForm[t[#2], 2]]], Dynamic@ If[Length@h[#2] > 0, Module[{z = Transpose[{Abs[#], Sign[#]} & /@ h[#2]]}, Graphics[ (Rectangle @@@ (Partition[{Accumulate[First@z],Last@z}\[Transpose],2,1,{2,2},{{0, 0}}] /. {{x1_, y1_Integer}, {x2_, y2_Integer}} -> {{x1 + 0.2, 0}, {x2, y2}})) /. {Rectangle[{x1_,0}, {x2_, 1}] -> {Darker@Green, Rectangle[{x1, 0}, {x2, 1}]}, Rectangle[{x1_,0}, {x2_,-1}] -> {Red, Rectangle[{x1,0}, {x2, -1}]}}, ImageSize -> {Automatic, 20}, PlotRange -> {-1, 1}]], "" ] } &, words], Alignment -> Left], Row[{Button[ "reset", (x[{#}] = 0; t[{#}] = 0; h[{#}] = {}) & /@ Range@Length@words], Spacer[10]}]}]] 

When my daughter asked me help with her spelling homework, for me the obvious thing to do was to write a Mathematica program for it.

The words:

words = {"lightning", "lightning", "cloudy"}; 

The code:

Grid[ Module[{x = 0, t = 0}, { #, Button["Start", t = Hold@AbsoluteTime[] - AbsoluteTime[]], Button[Style["\[Checkmark]", Darker@Green], t = ReleaseHold[t]; x++], Button[Style[ "\[Times]", Red ], t = ReleaseHold[t]; x--], Dynamic[x], Dynamic[Clock[]; ReleaseHold[t]] } ] & /@ words] 

Which produces this output:

So when I ask her a word, I click "start". Then I click ✔ or × if her answer is right or wrong respectively. I plan to keep track of time to answer, so the timer now shows how much time it took to answer.

So my question is: Why do I have to use Module instead of DynamicModule? For some reason the Grid command does not work if I use DynamicModule. On the other hand, if I use Module (as it is shown), then the syntax highlighter shows my "t" and "x" variables in red as if I am doing something wrong:

When my daughter asked me help with her spelling homework, for me the obvious thing to do was to write a Mathematica program for it.

The words:

words = {"lightning", "thunder", "cloudy"}; 

The code:

Grid[ Module[{x = 0, t = 0}, { #, Button["Start", t = Hold@AbsoluteTime[] - AbsoluteTime[]], Button[Style["\[Checkmark]", Darker@Green], t = ReleaseHold[t]; x++], Button[Style[ "\[Times]", Red ], t = ReleaseHold[t]; x--], Dynamic[x], Dynamic[Clock[]; ReleaseHold[t]] } ] & /@ words] 

Which produces this output:

So when I ask her a word, I click "start". Then I click ✔ or × if her answer is right or wrong respectively. I plan to keep track of time to answer, so the timer now shows how much time it took to answer.

So my question is: Why do I have to use Module instead of DynamicModule? For some reason the Grid command does not work if I use DynamicModule. On the other hand, if I use Module (as it is shown), then the syntax highlighter shows my "t" and "x" variables in red as if I am doing something wrong:

Update: I have just realized that using Module instead of DynamicModule is not a viable option as the scores are lost when you reopen the notebook.