Did you mean cylindrical? 
When running - or walking - on terrain, just take it slow and be careful how you place your foot. Awfully easy to turn an ankle, especially if you are not particularly agile.
And I was never into radios, gear, etc. Just shoes, socks, shorts - shirt optional!
I would have a piece of paper with my name/contact info on it in case I got hit by a truck. And I bought a fluorescent web vest for visibility if running in dusk/dark.
Stretching - you can drive yourself crazy as to what stretches to do, or even whether better to stretch before or after. I’m no expert, but I’d suggest you let your body be your guide. If you are running relatively short distances at a relatively slow pace, I’d suspect a lengthy pre-run stretch/warmup is not terribly necessary. I’d probably try to do a little stretching after. IME, you’d feel the effect on the 2d day after, rather than the next day. One thing that worked for me was to stretch when I had the TV on. If I didn’t want to stretch, then I didn’t turn on the TV. But if the damn thing was on, I had to be stretching.
Like Tony says - don’t try to do too much too fast. Not only could you hurt yourself, but you could really turn yourself off of it. Everything I hear says a brisk walk can be essentially as good as a jog.
Whatever you do - tunes/phone/a.m./p.m./streets/parks/etc - the most important thing is making exercise (and good diet) a part of your lifestyle, rather than something optional tacked on, to do when you feel like it. That’s one reason first thing in the morning works well for many. Don’t give yourself any option. You roll out of bed, and you hit the streets, before you even wake up and start coming up with excuses.
For me, I swim at a pool on my way home from work. I’m already in the car, and it just means I get home 45-60 min later than if I headed straight home. Personally, I have to think of it just as a routine part of my day - a priority/necessity, like showering, brushing/flossing, etc. Because as soon as you think of it as an optional recreation, you’ll find ways to convince yourself that you’d really rather just read a book, watch some more TV, surf the web, … In reality, you can do all that. Just make sure you do your exercise in the slot you carve out for it.
(I’m sure there are some more disciplined folk than me who can simply exercise whenever. Hats off to them.)