Forget Iwb, your pants will be on the ground by the end of the block. pocket can be problematic too, this is one if few times I will pull out the old shoulder holster.
Ultimately what works and what does not is a very individual decision.
Fanny packs work for some and seem to be fairly common for joggers.
An IWB with a sweat shirt or long wind breaker. Suspenders can help with the sagging pants.
For years I ran cross country with a padded holster (Uncle Mike's?) small-of-back, with a leather belt on the outside, tightly cinched to prevent chafing and to keep the load (gun, ammo, & knife) from bouncing. A really long shirt conceals everything pretty well.
Used to use a web belt with soft holster. No longer run CC but do jog a bit. The little Colt 25 was not much but better than nothing. Would probably use a Keltec or LCP in 380 now.
There is a manufacturer that makes a crotch holster just for the purpose of running. It is like a fanny pack but the pack puts the gun inside your pants just below your belly button and above your junk. It has a wide web belt and quick snap clip for on and off.
Sounds like you have lots of options. Myself I like IWB at 3:30 wearing shorts or jeans, and a fanny pack with sweats. I would suggest carrying a fanny pack or a small backpack as a backup plan. Nothing worse than getting out in the middle of nowhere and finding out the new carry is not what you expected.
I can barely walk at this point due to a motorcycle wreck a while back, and I didn't run before that, But I could see having good success with a shoulder holster and a really light jacket. Beware of a sweaty t-shirt showing the outline of the shoulder straps perfectly.
Try a belly band. Under a tshirt and itvwould be great. I think the key here is having a light weight gun.
I am getting a PF9 & I have a air weight .38 just for those reasons to use with a belly band or kangaroo holster while jogging. Nothing else seems like q good option.