There are a ton of reasons to go for the masi(its a great bike, get it) The one Im going to tell you all about is the belt drive of the district. Its an awesome technology, a very low maintenance, long wearing part that is the first thing to go on an average bike. Chains don't last on the casual everyday commuter/bike path rider. Its perfect for that type of bike. But it is a real hindrance for some one that does more than commuting/ path riding. It doesn't allow for altering of gear ratios, and it cannot be swapped for other chain rings or cogs. It also seems like between you and your dad you will be able to properly maintain the chain of the masi.