Pro Tips for Infrequent Travelers

I've logged 3+million miles over the past few decades just on American Airlines alone! Along the way, I've figured out ways to minimize suffering, surprise and discomfort in travel planning and execution. It will take more work pre-flight, but will save stress, confusion and wasted time searching while still providing flexibility. 

• Reservations: make flight, hotel and car reservations early - check car and hotel closer to time to see if rates have changed. Avoid pre-pay hotels and car reservations in case of cancellations, to minimize 
• Give an extra day for arrival if any "events" or important reservations - in case of cancellations and delays - especially for overseas or "super special" events (like weddings, etc.). Also, pre-think potential alternatives - like different departing airports, connecting cities, airlines, or cars instead of planes, etc., so you're not caught by surprise when there's a major upheaval. 
• Make dinner reservations on OpenTable, Resy or The Fork (Europe) before leaving town - you can always cancel last minute if you make a new discovery and want to change plans (avoid cancellation penalties in these apps unless you're absolutely positive you won't need to cancel or change). 
• Search Travelocity (or similar) for flight/hotel inspiration - book direct for peace of mind that your reservation goes through. This also comes in handy if you run into a snag and need to change or cancel something. Increasingly, companies are referring people to the booking source if it's a "third party" booking. Airlines are starting to get more restrictive on ticket features booked through third parties. 
• Look at Airbnb for culinary and other tour "experiences" to get to know a city on foot or by bike. There are also other companies like Viator, etc. that offer bookings. 
• Avoid connecting times on flights less than an hour - taxiing, debarking, and other delays will compress that window - leaving little time for getting to gates, stopping for food, bathroom, drink, etc. 
• Be nice to gate agents and hotel clerks. They can reward you or be less than helpful depending on how you treat them. Chances are, the problem you have is not their fault, so look at them as an ally, not the object of your frustration. 
• As much as possible, concentrate flights and hotel chain stays to maximize loyalty points and perks, even if it costs a little more in the short term. Airlines are starting to really crack down on the un-loyal traveler: flights for no points, pay for seats, pay for checked bags, pay for changes, etc. Loyalty pays (at least so far) in terms of better seat options, free baggage check, priority in upgrades and cancelled flights, flight rewards, customer service numbers, etc.). 
• Though I break this rule on the time because I'm trying to squeeze so many places into one trip: Try to stay in the same hotel/location for at least two nights (allowing for potentially three days of exploration). Less than this and you'll feel like all you do is re-pack your bags every 18 hours or so. Even better, spend a week or more in one "hub" location and take day trips requiring no more than an hour or two each way by car or train.