Recommended tools for the astute travel hacker

All of these tools are very functional, even if you don't get the paid versions. I personally subscribe to Seats.Aero and I may add TripIt if I book a complex international trip.

1. Travel Freely - Free. If you are going to pursue this hobby, you need to be able to track your credit card sign up bonuses and renewals. With 30+ active credit cards at any given time, I depend on this free tool. Web and mobile.
2. PointsYeah - Free and paid. Very nice search engine for award availability including both flights and hotels. The free level is very powerful and fulfills my needs. Web.
3. Seats.Aero - Free and paid. This is my "go to" app for finding award flights. Free version is OK, but I sprang for the paid version after the first week (and I am cheap, so that says something). This is one of the most powerful search engines for award space. Subscription price is $9.99 per month or $99.99 per year. The ability to look for award space up to a year out and set notifications for award availability makes this app more than pay for itself. Highly, highly recommended. Web.
4. AwardTool - Free and paid. I find this tool works almost the same for me as PointsYeah. A more in depth review will be made in the future. I would use it in the free mode and then graduate to a paid seats.aero account when appropriate. Web.
5. Seatmaps - Free. Are you flying first class on a Boeing 737 or an Airbus A350? Find out what the seats are like (recliner, lay flat, milk crate) to help select what you should book. I am still new to this tool as I was using SeatGuru (recently decommissioned). Seems pretty nice, though and it is free. Web.
6. Aerolopa - Free. Another free tool for seat information. Nice graphics and a lot of information, but not as powerful as Seatmaps. Web.
7. Air Miles Calculator - Free. When award points calculations are based on distance, this comes in handy. Web.
8. TripIt - Free and paid. Polished, free application for organizing your itinerary. The paid version has some incredible additions, but the free version does a lot, too. If you have an upcoming itinerary that is complex or travel a lot, I would investigate the paid version. In the paid version, one of the features is their proprietary algorithm that can predict flight delays before the airlines notify you. This can mean the difference between you easily booking another flight or competing with everyone else once the delay is public. Web and mobile.
9. Google Flights - Free. If you are looking for a cash flight or just want to see what carriers service the route you are interested in, this is a great tool. Sometimes a cash option or even pay yourself back with points is better than a straight up point redemption with a carrier. I don't collect Frontier or Spirit points but I often take short, overnight trips from LAS to PHX for MLB games. It can make sense to fly on these slightly uncomfortable yet cheap flights as the duration is so short. The hotel search engine can come in handy, too, for cash stays.
10. FlightConnections - Free and paid. Great for visualizing airline routes. It lets you know what routes an airline flies or you can search a particular route and see what airlines support it. Does have some pesky nag screens if you use the free version, but it is still serviceable.