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[RC] foot pain - Melinda Faubel

Long time lurker, first time poster....
 
OK - I have to do something!  I've done a few 50 milers and everything has gone PERFECT - except for my foot pain. 
 
Here's some background:  I have a normal foot with medium arches.  My forefoot is not narrow, but not considered wide (for you runners out there, I run my marathons in a pair of Saucony Triumphs and I love them, so that is the shape of my foot.).  I was diagnosed with Mortons Neroma in on my of feet a couple years ago, but it hasn't bothered me much since. 
 
Here are combinations I have tried and the result.  Does anyone have any ideas?
 
Terminology:
Ariate boots - zip up paddock boots that are ankle height
CW stirrups - a wide, wooden stirrip with leather hoods
Riding boots - leather sole shoe with a square (roomy) toe box
tennis shoe - Saucony Trimph (had about 400 running miles on it, so it was "retired")
 
What I have tried:
Ariat boots+fillis irons = arch pain
tennis shoes+civil war stirrups = arch pain
riding boots+civil war stirrups OR EZ ride stirrups = numb feet
 
So I think the issue is if I wear shoes that are too flexible it inflames my arches, and if my stirrups are too wide, my feet go to sleep.
 
I'm thinking maybe geting a pair of inserts for my boots and keeping an eye out for a boot that might work better (not seeming to have much luck with ariats).  Maybe I'll try the easy ride stirrups again, this time with inserts in the boots to try and take even more pressure off....
 
So - somehow I need to find the right combination of boots, maybe inserts?, and stirrups!  why does everything have to be so complicated!  I want to know...what combinations of shoe/insert/stirrup/other do people use here?  Can anyone reccomend a shoe that I can ride it, but is also comfortable to jog in?  Would a trailrunning shoe have a stiffer sole and give more support?  Any one have any luck with shoe inserts?
 
Thanks,
 
Melinda