Personally I mostly use Google Flights for flight search (or seats.aero for award travel search) and booking.com for hotel search, and then book directly. I've booked probably 100+ hotels through booking.com and then quit entirely after hitting that long tail bad experience.
[1]: I'm a few years out of date on this and don't know the current legalities, but major OTAs (Booking.com and Expedia, who control probably 80-90% of third party hotel bookings) used to have a "most favored nation" clause that prevented hotels from advertising lower prices through other channels without a previous commercial relationship. Signing up for a loyalty program qualifies, so being logged in for direct hotel bookings can sometimes get you cheaper room rates. (In the US, things like AARP and AAA memberships also work.) I know the EU was pushing back on these clauses but I'm not clear on what the current state of things is.
OTAs can play "member" pricing games too I think so there's even better deals to be had.
So you definitely need to comparison shop, I make my agent take the pricing from all the OTAs and calculate a post-rebate price, then pick the lowest one.
You are still overpaying when using Amex/Chase/Cap1 portals.
$105-110 book on Amex/chase/cap1 portal
$101-102 after 5-8% travel portal cash back
versus
$100 book direct Hilton/marriott/IHG rate
$96-97 after 3-4% cash back everything card.
Don’t even get me started on “premium programs” like Amex FHR, Chase Edit, etc. Probably overpaying by $100+/night. Much cheaper to just pay for 4 pm checkout. And early check-in is dead anyway.
This hasn't been my experience. I usually search through Booking.com and when I contacted the hotel directly, found that the direct rate is higher than the booking.com rate.
Just a thought but I guess if the airline web services were overwhelmed with noise, they wouldn't be able to do such price adjustments reliably. The only risk is that this might bump the prices for everyone and it will turn out that consumers are not price sensitive enough to force airlines to not do this.
I remember examples of round-trip ticket A-B-A costing $x in A, $x/2 in B (plus another fare for country C) for some city pairs, but I don't think this has really been a thing in a decade at least.
Bonus points I'm not booking through shady websites like Expedia.