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The front mudguard, built out of what seems to be flexible plastic material, recently cracked and needs to be either repaired or replaced.

A friend of mine works at a car body-shop, and offered to fix the mudguard by attaching fibreglass on the inside of it. This sounds very attractive, since the stock replacement parts for the mudguard cost roughly 15% of the value of the motorcycle.

Is this solution (or another repair solution) likely to work?

I can imagine that the constant shaking and bombardment with road debris might cause the plexiglass to crack and/or dislodge, but don't know whether these are valid concerns. If repair is likely to work, what should I look for in the fixed mudguard to make sure that the job was done well?

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The plastic material is often one that doesn't bond (ABS, I think) that well with fiberglass (I assume you mean fiberglass, plexiglass doesn't make much sense as it's a transparent and not very flexible plastic) and you have to be very careful how many layers of FG you put on as most mudguards are running pretty close to the wheel. If you factor in the expansion of the tire at high speeds you probably don't have much space to play with. Oh, and don't forget that fibreglass will stiffen the mudguard, making it even more prone to breakage.

If I were you I'd hit ebay for a used mudguard in reasonable shape and get your friend to paint it.

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You could look at plastic welding: http://www.youtube.com/watch?v=D8rTwWRYb0c

If it's just a crack in the mudguard with nothing missing, this may well work well and is probably worth trying before hitting eBay (which is what I'd do next)

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