Join Date: Jan 2018
Location: Long Beach, CA.
Welcome. Here's my 2 cents for what it's worth. The first thing is to decide what you are going to do with the bike and be honest with yourself. Commuting-cruising-weekend riding-fast twisty riding with friends etc. That in itself will point you in the direction that you need to go. Do your friends ride and if so what do they ride. While it's noble to want to make your own path, being the only Harley in a pack of sport-bike riders will put you at a disadvantage as would a sport bike in a pack of Harleys.
If you think that either the 300 or 500 is a bike that you'll OUTGROW, then it might be best to start out on a used bike that you can keep for a short while and resell without losing too much money. For cruisers that might be the Rebel 250 and for sport bikes it might be the Ninja 250. Lots of them out there and at a fairly reasonable price.
Either way, rubber side down.
2019 Honda Shadow Aero 750, 2017 Honda Rebel 500 (SOLD), 2018 Kawasaki Vulcan S 650 (SOLD)