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It seems that no matter how well I stretch before a run I always ache from my mid calf area to my ACH (along with feeling very tight). And even stretching 2-3 times during the run doesn t alleviate the discomfort.

I know by this point y'all must think I'm falling apart from the knees down but I'm not sure if these discomforts are a result of years of inactivity or something I'm doing wrong pre-run.

Thanks....again....

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You just need to keep stretching both before and afterwards. Your body is protesting what you are making it do. You'll see less of it as time goes on. Again, ice and anti-inflams are your friends.
Your body will let you know if you need to stop. Remember, there is a difference between sore and injured.
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Along with what Coach said, wait til you just started to work up a sweat....that's a good time to stop and do some stretching (I nevah stretch before I run, but that's just me)...

But I think you're right, these symptoms might just be your body screaming at you...
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I'll preface this by saying I'm kind of a caveman about stretching. A couple things. One is stretching before a run is not too good. Your cold muscles aren't very limber and giving them a yank probably doesn't do much for you. The best time to stretch healthy muscles is after a warm up mile or after the run is done altogether. Second is, if you're already injuried, stretching is not the recipe for healing. Imagine pulling on a frayed rubber band. Yep, you just might cause more damage. Coach is right about the ice and ibuprofen, that'll promote healing.
The benefits of stretching are largely in injury prevention. So once you're healed up, keeping flexibility with stretches is going to be a weapon in your arsenal against hurting yourself. But once the damage is done, you really need to step back, ease down and heal up.
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:1:
Cavewoman here.
:1: :1:
just call me Zog.
frustrating as it was, when i had a chronic hamstring pull, i was told over and over by MDs and one PTs to stretch it. stretch it long and often. i'd tell them i think stretching "AGGRAVATES" it--they'd insist it was over tight and needed stretched. :x as soon as i stopped stretching it, it seemed to mend itself in a matter of weeks.
less is more with stretching.
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You may not want to listen to this but I never stretch before a run, post warm-up or no. It just feels wrong and then I feel all weird running immediately afterwards. Of course, that said, I have like a 15 minute post run almost yoga routine that I do religiously or my various parts start barking at me.
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I always warmup after my second mile (18 mins) warming up first. Your stretches are most important at the end of your run. When I stretch first it slows my runs down every time. Never, never, never, when?, never stretch beyond any discomfort much less pain.
Always warm down to circulate the blood and decrease the risk of heart stress and heart attack.
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I'm with you, pffff. I never stretch. To warm up I always do a very soft run (read: jog) for 5 minutes.
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