Injured Cyclist turned runner, have a lot of questions!

Plantar fascitis is typically incurred by overly supportive shoes / orthotics, and achilles tendonitis is typically incurred by shoes with too little on the heel. You are typically best off with a lightweight trainer like those which were more common in the 1980s before the air and gel fad.

However in your case, with all of your twisted joints and what-not it's too inconclusive to really assess what it is you will need for your particular complex of issues.

Orthotics tend to be bad news unless they are perfectly fitted and you want to use those as a last resort only.

Cool down after workouts for a mile or two barefoot on groomed grass if you can find it. This will strengthen the connective tissue in the feet and really helps resolve plantar issues.

Also get some serious massage work done on your calves as tight calves tend to lead to both of these maladies.

I would definitely ditch the orthotics and the stability shoes. Have you considered running in Vibram Five Fingers or a very lightweight training shoe? I would definitely look into those. If you do decide to stick with the orthotics though, definitely wear them when you walk too. Personally I'm really not a believer in orthotics in most situations.

If you do have a right calcaneus SFx, you'll probably end up having to take off 4-6 weeks at a minimum. I had a calcaneal stress fracture a few years ago and I was in a boot and on crutches for the first 4 weeks. I know its a giant pain in the ass but I would definitely use crutches for a little while. I started running again after 6 weeks, and started very, very slowly. Also, do some PT exercises to strengthen the ankle flexors and extensors once you are out of the boot. Its definitely normal to feel pain even if you're not heel striking, the calcaneus is still bearing some of the load.

Being a long-term cyclist means you probably lost alot of bone density given that pro cyclists tend do very little weight bearing exercise. So it is no shock that you got a stress fracture when you started running

Your best bet to becoming a runner is to continue to cycle while building up the bone strength for your body to be able to handle the pounding.

1) stick with the neutral shoes. you didn't get the fracture because of the shoes, the bones in your feet just aren't strong enough to hold up to the pounding. Don't even think about going the barefoot route. at this point, you might as well take a big rock and just drop it on your foot.

2) Embark on a overall strength training program that includes squats and core. Use heavy weights where you can only do 8-12 reps. Strength training has been shown to build bone density

3) Your return to running should be done following a ride like a triathlete. Start with going for a long hilly ride then jump off the bike and run for 20 minutes. Continue to decrease the ride and increase the run each week. since you are a competent cyclist, you probably won't get the "brick" feeling that many triathletes speak of.

4) eat calcium rich foods.

In addition to the foregoing about bone-density and such (about which I know nothing), ask around where you are for a knowledgeable PT or podiatrist. You may have a form issue. For starters, at least try a well-regarded running store (don't know the kind of store you went to) where you'll be watched (and videoed) running on a treadmill. There's nothing inherently correct about "midfoot/forefoot striking" nor anything natural about it either. Good luck.

You need to go see an orthotist. An orthotist can custom make soft orthotics (never run in anything with any rigidity) and compensate for the leg length discrepancy.

Otherwise, the above info on bone density is good advice. Generally, you have an aerobic engine that far outmatches the kind of pounding your body can withstand. Remember that Lance gave himself shin splints when he first ran a marathon. So, just go out and run easy in a shoe that feels good to you. Build up some mileage for a few months before trying to do workouts. And stop thinking about everything so much. Don't worry about form. Runners with great form get hurt too. Don't worry about shoes. Minimalism is not the answer to everything. For people with low arches, minimalism can be a bad thing.

calf drops for achilles, loosen laces or skip eyelets for top of foot pain, run SLOW and short on soft surfaces while you very slowly build mileage, given your injury history. Come back healthy at 30 to 40 mpw in six months or more and we'll give you workouts. Good luck harnessing the aerobic power you got from cycling.

I would recommend going back to cycling.