1. No.Three reasons not to trade...1.Big...2.Heavy...3.Ugly.
3. Subjective (but still no).
The 300 is a great bike, but it's an easy bike to outgrow. Most riders will eventually want something bigger, more substantial, and more powerful. If OP is thinking the time is right to make the jump to something bigger, then the time is right to make the jump to something bigger. This is the same natural process that drove me to trade up from the 500R to the 650F.