Okay, you already know about useful sites like TripAdvisor and SeatGuru, and you're doing your best to accumulate and use frequent-flier points. Here are some tips to cover the other stuff, inspired partly by my own misadventures.
The context for these tips is that I travel for public service and philanthropy, not business; I haven't been in craigslist management since 2000. (I hear that people travel for "pleasure" or on "vacation," which I understand are mythological concepts.)
Store everything online. Anything that has to be local, encrypt. Act as if you could lose your laptop anytime. Recently, I cleverly left my backpack in the cab taking me from airport to hotel, containing my laptop and medicines. The latter includes thyroid medicine, since I need it daily or I WILL DIE. (Slight exaggeration.)
As for forgetting the laptop, that's expensive, but I keep very little data locally (anything sensitive is elsewhere). Worst that could happen is that someone would learn my terrible taste in music and books…
Learn to do pretty much everything on the phone. Seriously, I can do almost all of my work on a smartphone, though some tasks are much easier on a laptop. Regarding your phone, store everything online. Accept that your terrible taste in music and books will become public. Always carry your phone in a pocket or somehow attached to you. For male humans, if the pocket thing doesn't work for you, learn to love the "murse." May have begun with Seinfeld…
Before you get to the airport, or inflight with Wi-Fi, check out your flight status. Now and then, I get a flight canceled with little notice. Sometimes that happens when I'm in flight, and my connecting flight is the problem. I use flightstats, which also seems to have the most current ETA. Even if you're at the airport, and they ask you to line up for customer service to get a flight, get on the phone while you're in the line.
Do good while traveling. Sometimes hotels don't have a preventive maintenance program, and you encounter a problem with facilities like the shower or A/C. Even if you'll be there one day and have to deal with it once, call hotel engineering anyway. (The next guest won't have to deal with it and will never know you helped, but do it anyway.) While you're at it, bring an extra charger and cable, and loan it or give it away to someone who forgot theirs.
If you happen to mix business with pleasure, be prepared to dodge drool.
Sometimes, I'll take a side trip and wind up in a family way. Pictured is the #20 nephew, aka The Kumquat. He's the one (visibly) drooling.
Oh, and if you're possibly getting married, and it's possible that they might have a chair dance planned for you, I recommend scotch.
Photo: creative commons licensed (BY-ND) flickr photo by ♔ Georgie R; selfie with Billy the baby