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One thing is it is definitely not possible to pull maximum value out of just having a CSR and doing all buying and reedeming through it.
Hotels you can do much better by redeeming through a travel agency which have their own rewards programs and cash back.
Flights you can buy with gift cards and attach airline cards for the bag fees. Bag fees of course are more relevant on longer vacations with multiple people. Short haul weekends not so much.
@Citylights18 wrote:One thing is it is definitely not possible to pull maximum value out of just having a CSR and doing all buying and reedeming through it.
Hotels you can do much better by redeeming through a travel agency which have their own rewards programs and cash back.
Flights you can buy with gift cards and attach airline cards for the bag fees. Bag fees of course are more relevant on longer vacations with multiple people. Short haul weekends not so much.
I am not at all sure about that.
Hotel travel requires using the hotel chain portal to maximize benefits in the hotel loyalty program, typically, not a third party portal. That being said if you're not a road warrior, a third party portal might be best. This is a case where a hotel loyalty credit card can sometimes be useful, if you travel enough where it makes sense (free nights in exchange for an annual fee, for instance). But for someone who wants to go all in on Chase, I think you could get away with UR to Hyatt or the Chase portal and do OK.
(I get what you're saying about portals like Hotels.com- though using Chase to pay that might work. Or using Chase for gift cards. However loyalty programs are tricky.)
For air travel, if you are redeeming in premium cabins (long haul international business or first), you get free bags. Gift cards are not going to go very far In that environment. Typically that is my pattern; pay cash for shorthaul, miles for longhaul (and get arbitrage since the miles price is more reasonable than cash).
I also go on multi-week trips around the world on miles (maybe a small sprinkling of cash tickets for short flights or trains in Europe). I also don't need checked luggage on those trips. Paying for someone to do laundry is cheap in a lot of Asia, coin operated laundromats work in Europe and maybe take an hour or two (time I don't spend waiting for checked luggage at a carousel). Even hotel sink laundry and a clothesline in a pinch. I can operate for a week+ at a time out of a carryon without breaking much of a sweat.