Kawasaki Ninja 400 and the Honda CB500F (if you stretch to find one in decent condition) tend to hold their value better than cheaper 250-300cc bikes, which matters when you're buying used. I picked up a neglected CB300R once thinking I was getting a deal, but worn chains, old tires, and engine sludge ate through my savings faster than just spending more upfront on something maintained. Before settling on any bike, pull the service records and check spark plugs, oil color, and chain condition yourself - a seller who won't let you dig in is already telling you something. The CB300 and Rebel 300 are beginner-friendly and parts are everywhere, but don't undervalue having a mechanically solid bike over just chasing the lowest price tag.