Chase Ultimate Rewards - Hotel Prices

[haasey]

I was trying to discuss travel hacking to a friend and wanted to prove that it was rewarding. 
I used my experience of booking 5 round trip (cheap) free flights on alligent so far as my proof.
So I asked him to tell me where he stayed before and I would figure out how many points it would be etc (exercise for myself to get more experience).
The hotel was a very swanky JW Marriott Marco Island Beach Resort.  My question is, have other travel hackers noticed how much the prices seem inflated on the rewards site to what you can book directly or find on google etc?  Not sure what to do about it, as the reason I am getting into this is travel.
My early findings are the airlines prices are spot on, but car and hotel prices appear more on the CUR site.
Thoughts appreciated for a newbie trying to take the next big step up.

[gocurrycracker]

As a general rule, the less flexible you are the harder it is to use points well. It's much easier to go where the value is than find value at a specific place on a specific day.

I've found booking hotels is almost always cheapest by transferring UR points to a rewards program and booking with points or points & cash.

And for the most expensive properties, it is most likely cheapest to use a card like Citi Prestige with 4th night free

Or maximizing hotel value via hotels.com
https://www.gocurrycracker.com/maximum-hotel-value/