This!
And if I have friends or relatives who have been to my destination, I sometimes ask them for opinions too.
Flyertalk is the gold standard for learning about loyalty programs. However, getting to the higher tiers requires a lot of travel, 40 or 50 nights a year, and the lower tiers don’t provide much in the way of benefits. With the amount of travel you listed, you’re better off just staying at whatever hotel gives you the best value for a given trip and not worrying about loyalty programs. Some Hilton credit cards will give one “free” night a year.
I also use google maps - but I use street view and walk up and down the neighboring streets (virtually) to see what the area is truly like. Works well in big cities - I picked an excellent hotel in Paris this way (the google street view was so good I could enter the hotel lobby and also see the specials on the chalkboard outside the nearest cafe.)
Google maps works great… Unless there is a new road construction nearby that is not reflected in the street view (duh!). 
I always open reviews and do “control F” “construction.” Only need to read the ones that have the keyword.
Thanks for all these awesome tips. Please keep them coming!
For me it depends what the trip is for and when/where it is. I will read the reviews on TripAdvisor but I also like to look at Fodors.com and Venere. As long as the location is good and the reviews and pricing work, I might choose either a Hilton or Marriott affiliate to gather points as sometimes you get upgrades or other perks for being a rewards member.
I favor Marriotts and Hiltons because I like their satisfaction guarantees, there are usually several of each to choose from when we travel, and I can almost always cancel on 24 hours notice without penalty. I think Hilton properties are generally a bit nicer (almost all their brands offer an in-room fridge, for example).
However (and this is huge for me), Marriotts are 100 percent non-smoking, while individual Hilton properties set their own smoking policies. I’ll always book a Hilton Garden Inn if the website says it’s 100 percent non-smoking, as many newer Hilton properties are. But if I’m not guaranteed a non-smoking room, I won’t book that hotel and will travel another 50 miles for a place that does guarantee non-smoking rooms.
We used airbnb when we recently visited London for 10 days. I was nervous at first, but felt safe enough about not being canceled on after reading the hosts’ many excellent reviews and seeing that they had earned a special airbnb designation (super-hosts?). In reading reviews for other properties, it seems that airbnb itself reports when the host cancels on short notice; it’s just a 1-line sentence stating that the host canceled. I seem to remember this, anyway!
Thanks for that reminder. H and I are extremely allergic to smoke and strong odors. I always prefer to book nonsmoking hotels.
Hilton keeps coming up so I will say we have been hilton honors members for 20 years mostly because they range from Hampton Inn on the road with free breakfast to downtown Hilton’s.
Oh, one other thing I always do - make sure that the property is not a Trump hotel. My personal preference.
I guess I flip-flop a lot. We do like Hamptons and Courtyard by Marriott better than the Hiltons and Marriotts. I don’t normally stick with any one brand enough to get nice perks at any of them. 
Oh, it’s so easy when the most important question is “do you allow dogs?” and then “do you have a per night per dog charge?” (because sometimes they allow dogs but the charge is $25/night/dog and that adds up fast!). On one trip, we ended up in a suite at the Four Seasons in Vancouver, BC because they a) had two beds for the kids in the front room, b) allowed dogs, c) didn’t charge extra for dogs, and d) were running a special. It was, quite seriously, the cheapest place in town for two adults, two kids, and one dog. And the dog got her own bed, bottled water, and treats.
Edited to add: my sister is not fond of dogs, and she asks “do you allow dogs?” and then doesn’t stay there if they do…
As a tie breaker I look at important details. Free wifi ( I have no idea why hotels charge for wifi in this day and age), free parking, free hot breakfast. Those items are important perks when traveling on business.
I stayed at a Marriott on Friday night…that is hooked to our convention center. I didn’t book the room…someone else did it…and paid for it.
But.
- The restaurant in the hotel cooks everything to order...which is lovely. BUT we put in our order at 5:15 and at 6:30 we still hadn't been served anything but salad and bread. Most of our party had to leave by 7...(and yes...we told them this when we sat down. Most of us took our meals in boxes...and left. They brought the food about 6:45.
- The walls were so thin...that I could hear the guy in the next room snoring.
OK, have booked a Homewood Suites. It’s across the street from a hotel that has a covered path to the convention center, which is two or so blocks away. The reservation can be cancelled up to 24 or 48 hours prior to arrival, includes free breakfast and wifi, fridge & mircrowave. Also have booked the convention hotel that will cost twice as much and will likely be canceling that reservation soon, no food, micro or fridge included.
When I travel to conferences, the organizers always offer special rates plus detailed information package including walking distances, shuttle service, guest programs etc. It’s always a very easy choice
For non-business travel, I always check reviews on trip advisor, and look for free hi-speed internet, complementary parking, and on site restaurants / room service in case I arrive late or too tired to go out
I had several bad experiences with Expedia when they lost my reservations or provided incorrect room or hotel descriptions. Therefore, I always call hotels directly. They help to choose the best room, answer any questions, and match the best prices I found on other sites (or even give better deals)
Yes, most of the conferences I attend DO have some information for attendees but not all of them and sometimes the conference rates are frankly about double what we’d prefer to pay for lodging. Also, sometimes by the time they give me my registration number, the lodging nearest the conference center has all been taken and I don’t always have the stamina to walk from the furthest hotels back and forth to the conference. When I attend conferences, mostly we are just in the room to sleep and not much else. I have mostly booked directly with hotels, as it seems easier to make corrections and adjustments when there is no middle party.
@HImom , Homewood suites is generally comfortable and spacious. Sounds like a good choice. (And having a real fridge, microwave, etc. can be nice if you are there for a couple days.)
Yes, will be there a week! Fridge is “nice to have.”
Absolutely fridge is good - need somewhere to chill the wine