This past trip I looked at a third party booking site (Expedia) where I got cash back and cheaper prices than on the hotel web site (I did use it to book the flights and got cash back via ebates).
I emailed the hotel owner and he matched the price AND upgraded us to a nicer room for me booking directly with him instead.
Win/win.
For Jamaica, I work with hotel directly because I keep a relationship with them - I'll reserve for next year when I check in this year.
For other travel, I'll get quotes both direct and from on-line sites.
in the 90s and early 2000s i would call hotels directly, but since the mid 2000s i email hotels directly.
specific to negril, i always go back and forth, back and forth, back and forth via email with the rude receptionists at xtabi (the only hotel i really stay in in negril, since 1995) and they always screw up my reservation.
i tried in december to book xtabi for february and they were so unpleasant i just gave up and emailed alfred's ocean palace and bernard saulter, who owns cottages near seagrape (https://www.airbnb.com/rooms/15806208). both were so pleasant that i'm tempted to stop bothering with xtabi.
i also reached out to catcha gardens via email and they were SO nice and helpful.
I have used Onestop and boy they came I handy. Got to our hotel to find it was overbooked, and there were 12 of us requiring 6 paid for beach front rooms. Called bob and Susan, they were onsite in5 minutes and got us put up in a great place, safe and with full AI for the night, and then back at our original hotel the next day with room credits for all and our beachfront rooms as ordered. They are more than willing to go the extra mile, and they are just really great people all round. Have also done the returning guest at the same hotel discount. Whatever works and makes you happy, well, then it works, right! Life can be short so live for today with an eye for tomorrow and no time to look back
“One good thing about music, when it hits you, you feel no pain.”
― Bob Marley