Later today I am making the trek to go pick up a set of wheels and 35" tires. Will I be able to fit 5 of them in my jeep?
You can get it done at a dealer. Charge is usually $125. Many people use a Tazer (https://zautomotive.com/product-category/tazer/) - either the Lite or Mini will handle tire size changes. The Tazer can do many other things. Worth reading some threads on this site for some great information. Here is one example. https://www.jlwranglerforums.com/forum/threads/tazer-jl-more-than-just-a-tire-size-programmer.8746/Hey all you 35" guys, I will be joining the club. How are you all recalibrating your speedo?