Guide - There’s no way to do Jerusalem justice without a knowledgeable guide, especially if you have limited time. I highly recommend Meir More - I booked him for a full day tour in the city and left with everything I thought I knew shaken to the core and having learned so much more.
Hotels - The circa 1930 King David Hotel is one of the most iconic hotels I've ever stayed in, with one of the greatest hotel pools in the world. The seriously impressive breakfast buffet (something Israelis are known for) has a huge selection of local cheese, salad, cereal, fruit, bread, and more. Be aware of Shabbat, the Jewish day of rest, when most of the city shuts down (from sunset on Friday to sunset on Saturday)--including many of the amenities at hotels. The King David closes its fitness center and offers a very limited room service menu.
The American Colony Hotel is a beautiful boutique oasis - I love the peaceful central courtyard and stone cellar bar.
Tips: I saw much of the city with my guide. Some things I learned:
It was very nice to have a car rental to get around, especially with limited time.
Start first at the Mount of Olives for the best sweeping overview of the city.
Don’t miss the sensory feast at Mahane Yehuda Market, one of the best food markets in the world.
Enjoy shopping and strolling at the modern, pedestrian-only Mamilla Mall near the Jaffa Gate.
Though I didn't stay there, I loved the incredible view from the bar on the rooftop at the Mamilla Hotel - great place to watch the sunset.