The Free range from Nike are part of the new, minimalist approach to shoe design so the flimsiness is part of the design.
I think you should defnitiely try before you buy, as they would be a big change for most people without your added orthotics & poblems.
I use them on a treadmill but have decided to stick with a more conventional trainer for outside. They are certainly light though.
I would be careful. Nike free have no cushioning/ support and if you're injury prone they might be quite a big jump from what you're used to wearing. I'm a neutral runner and have never had any serious issues but I only wear them on short runs up to 5m. For longer stuff I still go with some cushioning. It's not to say they won't work for you but you should probably test them first and build up to wearing them which is difficult to do if it's the only pair of shoes you're going to buy.
I also have orthotics as I have such flat feet (I got the nickname flipper from a work mate) and had major issues with sciatica for 18 months. I have just got running again after being problem free for a year. I purchased Mizuno Kabracan's though these are more of a trail shoe.
I would highly recommend going to a proper running shop with your orthotics and use their expertise to get the right shoes. I tried several pairs on their treadmill before I found the pair that felt just right.
After all my problems, I am happy to pay that bit extra to get the right shoes and stop any further issues developing. Its a lot cheaper than all those chiropractor, physio and podiatrist bills I built up.
I have recently bought a pair of Nike Free 5.0 following recommendation from my physio as I have issues with foot mobility and support to arches etc.. but I only wear them for day to day stuff that I would wear normal trainers for (and they're super comfy) as I already have a set of orthotic insoles for my running shoes which I prefer.
I'd say test them out though and see what feels good but build up the mileage slowly until your feet get used to them.
Nike frees are like slippers. Unless you've good running biomechanics I'd go with a more structured shoe or you'll be swapping one set of injuries for another. Once you've conditioned your feet, calves etc you could do some shorter runs in them to see how they feel.
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