My question is how hard would it be to pass the technician class tests? I'm pretty well versed in theory and have done my share of homebrew.
Passing the Technician test should be pretty simple. The Morse requirements have been eliminated, so all you have to do is pass a 35 question test. You experience is great, but the Technician test is mostly about operating privileges, UHF/VHF operations, procedures, and equipment. The test is made up of 35 questions selected from a pool of 423 questions. Practice exams can be had on this site at
https://www.eham.net/exams and at
https://www.qrz.com/hamtest/. The question pools are the actual questions used on the tests.
KD0ZGW is correct about taking one, two, or all three license class tests in a single session. People do it all the time. When I was testing, before they dropped the Morse requirements, I took the Technician and General class tests in a single session. That included the 13 WPM Morse test. Then, a few months later, I took the Advanced and Extra class tests in a single session along with the 20 WPM Morse test. The only reason I waited, was to insure my Morse Code speed was up to snuff. The Advanced and Extra class tests are effectively combined now.
Note that passing the Technician class exam will only get you voice privileges on 10 Meters and all of the VHF/UHF frequencies. Plus CW privileges on 80, 40, and 15 meters. To provide yourself with the maximum flexibility while on your trip, you should take all three exams. The Extra class license will give you full privileges on all amateur bands.
Testing is usually handled by Amateur Radio Clubs through their VE (Volunteer Examiner) system. To find the closest place near you go to
arrl.org and do a search on "Exam Sessions" in your vicinity. I can see, for example, that the Tallahssee ARS gives tests at the local American Red Cross, every two months. If you require a mentor, the clubs should also have them available. Many clubs provide study classes for a levels.
Good luck with getting your license.