It's all personal, on the timing thing it is really personal, I used to be a proffesional athlete (getting back into it slowly), and I found that different exercises at different times, but I used to train up to 8 hours a day. So I got to try out lots of different times. The best for me was long distance in the morning, so about 5 am to 10 am, and speed work mid afternoon and weights in the evening, but this isn't as relevant to you.
On the how long/how hard sort questions, spend some time setting a bench mark, a distance/pace that you are comfortable with, if you can try and walk fast enough so you are slightly out of breath, but this depends on your ankle. Once you have that bench mark then you can build up from there. But make sure you plan your training, beware of just going out and having a bit of a wander.
Stretching, I am one of these people who swears by it. Without stretching you may find you suffer from more muscle stiffness and more cramps. Muscles are made from lots of fibres, with out stretching these fibres will come to resemble a bag of wool after a kitten has been in it, this will restrict movement and reduce the ability of your body to remove waste products, stretching will straighten these out and lead to longer leaner muscles.
How to stretch, two schools of thought here, some swear by 20-30 minutes stretching before you even step out the door, others don't stretch before exercise, instead spend hours stretching in front of the TV, I have always stretched for an hour in the evening (purely because it's a great excuse to sit in front of the tv and when people say can you just .... yell 'no i'm stretching) and also stretched for a few minutes before each training session, and also a few minutes after, also make sure you cool down afterwards. It sounds really daunting, but you can find that you build it in to your exercise without realising, for example I stretch out my calfs whilst finding the key to the front door, and I stretch my back whilst towelling down the dog (terrier so long way down). If you can buy a book on stretching, or down load something off the internet.
Running shoes, YES, you've got a weakness already in that you injured your ankle, they don't have to be expensive, my last pair of running shoes cost £15 in the sales, but with out them I find all my joints hurt like hell.
Sports Bra, depends again, I'm an F cup so I don't walkk without one, other women I train with are A cups and don't even wear one to run. I'd say yes all the time, as normal bras don;t wick away sweat and all the nastys that exercise can cause.
Eating before exercise. Well the reason people say no is that digesting food takes blood away from the muscles. And can cause cramps if you don't get it to the digestion. A point here, meat takes the longest to digest, and this tends to be the cause of cramps and sluggish feelings. This is not really an issue considering what board we're on. In general it is recomended to eat 20-30 mins before exercise, with out this you wont have the energy stores for the first 20 mins of exercise before your body starts to tap into it's fat stores and may struggle and start to metabolise muscle instead, yes this lead to weight lose, but the fat stays were it is. Take something to snack on whilst your out, a bottle of water is a must, mix in a little fruit juice if you think it will make you more likely to drink it, and something easy to snack on if your out more than 20 mins.
Sorry about the essay, but I coach evey week and I hear the same problems every week, 1) I hurt the next morning, (Not warming up and down and not stretching) 2) I got bored, (take along an MP3 player, or little radio, or even better a friend) 3)I couldn't be bothered, (make a plan and stick to it).
Hope this helps, PM me if you have any other questions (except the have you got a life question, the answer is no).