Once I decided I was going to take my Ham exam I downloaded the
No Nonsense Technician Study Guide read through it then used
Ham Study to study. In my opinion the Hamstudy.org flashcards are hands down the best way to prepare for the exam. the algorithm ensures you see all the questions in the pool, offer explanations for most questions, and keep track of your aptitude. After taking and passing my exam I got an easy to remember vanity call sign.
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My First Radio was a Kenwood TM-281 tied to a Nagoya 1/4 wave magnetic antenna. For trail duty this setup is perfect and is no more expensize than most CB setups.
Kenwood TM-281a
NA-771 Nagoya
After getting into the hobby I switched to a Kenwood D710 which allowed my to do dual watch/dual receive and get into APRS for vehicle tracking. This is an expensive radio, and is not for everyone, however it does everything.
Kenwood D710GA
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For anyone looking to get into Ham Radio primarily for trail use I would recommend the Icom IC-2730a. The benefit of this radio over the Kenwood TM-281a is it is a true dual bander and can monitor two stations at once this is useful on the trail to monitor a simplex and repeater at the same time.
Icom IC-2730a