My brother's 375 doesn't seem to like starting these days. It seems we need to turn it over forever before it finally catches. Then it takes a few more tries before it will keep running. It does this pretty much regardless of choke position. Once started and warmed up, however, it seems to run fine.

Any idea's what could be causing this?

 

Sounds like a spark issue....

 

You might want to have the compression tested at the dealer. Classic symptoms. Had 2 bad rings on my 03' with about 50 miles on it.