Solution 1:

I was smart before writing this huh... I only used one generator to try and make the command. As soon as I posted this I was like "hey lets try another one" and it worked. This is the working command:

/blockdata ~ ~1 ~ {Text1:"[{\"clickEvent\":{\"action\":\"run_command\",\"value\":\"/execute @p[score_wins=24] ~ ~ ~ /tellraw @p [\\"\\",{\\"text\\":\\"[MF2] \\",\\"color\\":\\"gold\\"},{\\"text\\":\\"[SHOP] \\",\\"color\\":\\"yellow\\"},{\\"text\\":\\"You do not have enough wins to upgrade your sword.\\",\\"color\\":\\"none\\"}]\"},\"text\":\"\"}]",Text2:"[{\"clickEvent\":{\"action\":\"run_command\",\"value\":\"/execute @p[score_wins_min=25] ~ ~ ~ /tellraw @p [\\"\\",{\\"text\\":\\"[MF2] \\",\\"color\\":\\"gold\\"},{\\"text\\":\\"[SHOP] \\",\\"color\\":\\"yellow\\"},{\\"text\\":\\"Sword upgraded!\\",\\"color\\":\\"none\\"}]\"},\"text\":\"Upgrade Sword\"}]",Text3:"[{\"clickEvent\":{\"action\":\"run_command\",\"value\":\"/execute @p[score_wins_min=25] ~ ~ ~ /scoreboard players add @p sword 1\"},\"text\":\"25 Wins\",\"color\":\"green\"}]",Text4:"[{\"clickEvent\":{\"action\":\"run_command\",\"value\":\"/execute @p[score_wins_min=25] ~ ~ ~ /scoreboard players remove @p wins 25\"},\"text\":\"\"}]"}

Well, I guess that solves that.

//Edit: The link to the generator I used is by MCtoolBox, and you can go straight to the sign generator by clicking here.