Both my husband and I used to backpack in these boots…
Use: medium-heavy backpacking in mountains
Break-in Period: short
Price Paid: ?
Both my husband and I used to backpack in these boots back when we were poor college and grad school students 20 years ago. So some of the features I mention may have changed. As I recall, the main reason I bought the boots was that they were cheaper than better backpacking boots and I could wear them around campus during bad weather without the "clod-hopper" look.
These Timberland boots are really work boots, not backpacking boots, although they do offer more support than lightweight hikers. One aspect that I hope they changed is the tanning of the leather liner which bled into our socks staining them bright orange and the cuff stained our socks brown. I think my boots were not "waterproof", so the leather got too soft when wet, so the toe got stretched out of shape after being worn in the rain. (Maybe someone with wide feet could purposely stretch them to fit that way, but I have narrow feet, so the boots just got too roomy in the toe box.) I did wax and silicone them, but the leather was never really waterproof. However, I vaguely remember that my husband's boots were more waterproof, so maybe I had a cheaper non-waterproof model. No gussets around the tongue meant that water would really leak in and soak my feet.
My boots lacked any molded insole. I think I added a thin Spenco insole, to soften the hard leather footbed, but I have narrow feet so there was room. The footbed was flat with no arch support. Even though the boot was cut fairly high, the ankle support was only so-so. That was a problem for me since my ankles are unstable due to multiple ligament tears when I was a high school runner.
I now use a pair of old Italian-made Vasque Sundowners. I think they may be lighter in weight than my old Timberlands and they give much better support and are more comfortable.