Gershon - your advise is wise

What is challenging though, is when you complete a hike/walk, and at the time feel no pain. Then you wake up the next day with pain. This was the case with me and my achilles a couple weeks ago. And I did adjust my hiking distance the following week (down to 1.5 hours and slightly less technical terrain), but in minimal shoes that never bother my achilles. Result was no pains afterwards.

I guess with my winter hiking boots I'll need to go out for maybe a 1hr hike and then monitor during and after for any pain. If good, I can increase next time.

Here's the thing that makes me shake my head...I'll go with the family to an amusement park and walk for 6-8 hours (not continuously, but I am on my feet 99% of the time). I'm tired after, but never in pain. Sure it's not technical...but when I'm on technical terrain I'm "trying" to wear suitable footwear, but then maybe it doesn't actually make the terrain less harsh on the body?

I'm sure I'm over over-thinking it, but it's a little frustrating when you want to be involved in an activity, and one that (where I live) doesn't on the surface appear to be too challenging, and you're held back by issues that don't crop up anywhere else.