I think these two make a good duo even if they are not quite shipped together, but now we have two clumsy horses and as a bonus he's even bigger than the Big Mac of the Apple family!

How would these two get along?

Hmm. I honestly surprised to not thought of this pairing before. They are both ridiculed endlessly, accident prone, destructive behinds, have stand out unique appearances, and just want to enjoy life, despite their hardships. If they were to meet it would probably start off rough, (due to their conflicting perspectives Derpy being an optimist while Troubleshoes is a pessismistic one), only when that is dealt with, then could it gradually blossom.

Their professions and choice of residences would be an issue though. Especially if one were to add Dinky and Amethyst Star/Sparkler were added to the equation. Good lord their possible offspring would either be the most unfortuate soul, doom all of Equestria, or their fortunes effectively cancel eachother out to produce a possible messiah of pure positive chaos and herald a new age of prosperity. Silly ramfications aside, if its well written enough I would read it. So "ship it" I say!

I already began shipping Derpy and Trouble last night because honestly, the ship could work very well. They both have quite a few similarities and such. It would also do Trouble Shoes some good if Derpy was around him, since she's a little clumsy as well and that would help ease the poor guy.

It seems that some other people like this pairing as well, on DeviantArt at least.

Yup, I definitely ship this. It's just way too adorable and interesting to pass up