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Guys with your sister will generate really weird feelings in you. We are all conditioned to protect our sisters, for good or ill. If your friend is a really great guy, and it all works out, then BINGO, you can have a cool brother-in-law.
But, how often does "it all work out"?
Then, when it crashes, who's "side" are you gonna take? You can lose a friend this way. Or not.
I had a buddy from high school who was really promiscuous in college. He had the hots for one of the sisters of a mutual good friend of ours. The guy, our mutual friend, straight up TOLD our "player" friend to leave the sister alone. I'm pretty sure he did (though we likely will never know.) Hard feelings and broken friendships can come from this kinda stuff.
I guess you just have to weigh out how pissed the friend will be when his deal with your sis crashes.
(And, given the odds, it most likely will.)
You then pay your money and make your choice.
The INVERSE of this, however (girlfriends of your SISTER dating YOU) is a GOLD MINE. For some reason, a different mindset is involved. I've enjoyed this kinda thing a LOT, and no one seems to get hurt. But it's fun.
Wonder why it's so different?
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