Please Help if you can

I have a 2000 yamaha V-Star 650. When i go to start up it trys and trys but takes forever to start. Once its running im fine but if i cut it off and let it sit for like a half hour its back to almost impossable to start. I changed the spark plugs and fuel filter but still the same thing. Also While riding i hit 55 mph shift to 5th gear and it sounds way different then all my other gears. kinda like a whining sound, didn't know if this was normal since this is my first bike. Any help would be appriciated more then you know..... Thanks