I have a very old black tweed Hartmann 26-inch case that I inherited from my grandmother. It's my most prized piece of luggage (and I have about 8 sets of various brands). I bought a black 21-incher and shoulder tote to go with it. I'm glad I have the pieces, I couldn't afford them now.

I use the Hartmanns for car trips only, for instance if I'm going to Las Vegas and staying at the Venetian or similar. I would NEVER check the tweed or matching black bag and always worry about dinging up the carry-on bag. I can sympathize with the woman who had to gate check her Hartmann, painful. I say never take a carry-on you wouldn't be willing to gate-check in a pinch.

Yes, people are judged by the luggage they carry, but most people in airports don't know enough about luggage to notice. I always take note of people with Halliburtons, Tumis, etc. Keep in mind that thieves (sadly this includes airline personnel) look for high-priced luggage as targets. I always travel by air with luggage from Skyway, Columbia, Travelpro Walkabout. I don't want my luggage to stand out at all.

As to whether the OP's bag is "worth" $300, if you can afford it then of course it's worth it.