Yeah, I don't think owners who underinsure have any room to complain. I know I wouldn't, it's an agreement with terms clearly spelled out. And if you do it, it's a gamble. Frankly, if I ever accrued 250k of hull damage on my plane from flying (the amount I wanted to insure it at), I would just assume the plane repairs are the least of my worries. With that amount of damage done I'd be fine if my surviving beneficiaries handed the keys to InsuranceCo and let them buff my blood stains out of the cabin and resell it. Unless the DuPage hangar tips over, or I crash my car into it at 20mph -- I don't see myself ever collecting on that amount of hull damage. Liability is what really matters to me. W.r.t your advice on waiting and flying the arrow more before moving up, it's something I'll have to consider based on my insurance options and the plane market in general. But I really do want a platform that is already equipped well for IFR and longer XCs. As much as I love my plane, and I really do, it's just not ready for that unless I pour a bunch of money into it (e.g., need a GPS unit $$$, replace currently unreliable AI with G5 $$, get rid of vacuum pump, etc). I'm reluctant to do that when I know I'll be jumping ship to something speedier and more modern in the very near future. But we'll see how things unfold, it may work out like that anywho.