I'm the OP and after thinking about it, if it were my airline I would show a fee calendar during award booking with the fee windows clearly colored as the travel date approaches. Keep the Award availability window as it is, but just make the award booking fee for non-EXP's clearly visible in calendar form.

An email reminder the day before penalty fees apply, but before HOLDs expire, would be also be great. On that topic, is there an email reminder of HOLDs expiring? That would be nice too for any type of booking. Thanks all.