Everything arranged before departure.
Plan redemptions around a floor value of roughly 1.2 to 1.5 cents per mile in economy — book the moment award space opens, keep balances transferable, and never let miles substitute for a fare you would not pay cash for.
An open-jaw ticket — fly into one city, home from another — typically costs little more than a simple round trip and saves a full backtrack day; price it against round trip plus budget carrier legs before deciding.
A standard policy bundles trip cancellation, medical, evacuation, and baggage cover for roughly 4 to 8 percent of prepaid trip cost — and cancels for a narrow list of named reasons unless you pay extra for CFAR.
Price the three fixed costs first — transport, lodging, intercity moves — then set a daily rate for everything else and add a 15 percent contingency; a one-week US trip for one lands near $1,500-2,500 by that math.
For a single-ticket itinerary, plan at least 60 minutes for a domestic connection and two hours for international; anything booked as two separate tickets needs an overnight or half a day.
Midweek departures — Tuesday and Wednesday — consistently price below Friday and Sunday flights in Expedia and Google data, often by double digits, and shifting your dates is worth more than any booking-day trick.