Ive only had my Prestige for a month now and was already able to get about $ 900 value from the benefits offered not including the the 50K TYP.
Im travelling to South Africa in December and I was able to use Citi Concierge to book my 4 night stay in Cape Town and get the 4th night free which is worth $ 520 a night.
I also used the $ 250 airline credit for my short flight from Johannesburg to Cape Town. Used the $ 100 Global Entry credit as well.
My understanding is that the 4th night free benfit can be used an unlimited number of times but only once per reservation.
If you travel even just once a year for atleast 4 nights covering the annual fee should be easy.