Hi Smackduc
I wouldn't like to see myself in swimming gear!
Anyway, first question - best time to run. Whenever suits you. It's as simple as that. I enjoyed running early in the day - it gives you a good feeling for the rest of the day, but the important thing is simply to run and enjoy it.
Running to get fit is relatively simple and cheap. But you need to be properly prepared and organised to get the most out of it, both in terms of enjoyment and in fitness. A few tips:
1: Proper running shoes are a must. Running is a high impact exercise putting terrific strain on things llike knees, ankles and spine. The correct shoes will reduce the risk of injury.
2: Allow enough time in your runs to warm up and warm down before and after each session.
3: Check that your neighbourhood is a safe environment to run in.
4: Write yourself a weekly running schedule which enables you to gradually get fitter and fitter - I've put an example below.
5: Be realistic about your objectives. Be patient, build up your stamina slowly.
As you run more, you will get stronger, faster and more confident. You will lose a little weight (the amount depends on how far and how often you run but I would stress the need to be patient), and you will feel generally healthier. Eat well but sensibly. Drink plenty of water. Maybe you could also do other exercise to combine with your running like swimming or cycling.
Here's a basic four sessions a week schedule which might help.
Session 1: Use this for your 'long run'. This is the generally accepted way of building up your endurance. To start with just measure how far you can jog/walk (as slowly as you like) without getting out of breath. Whether it's 1k or 5k, it doesn't matter. Just build up from that, gradually increasing the distance week by week but keeping to the same pace. When you can slowly jog say 5k without stopping and without getting out of breath you will be well on your way to achieving a very good level of fitness and you will feel a whole lot better about yourself.
Session 2: An interval run. This is where you learn to adapt to different speeds. Jog half the distance as your long run but incorporate a middle section where you run slightly quicker. For example, if you jog a total distance of 3k, start with 1k slow, speed up for the next 1k, finish with 1k slow.
Session 3: Nice and easy jog/walk, slightly quicker than your long run pace but again only half the distance
Session 4:: Sprints run. Jog slowly for the same distance as in Sessions 2 and 3 but incorporate some sprints - let's say 4x50metres, giving yourself time to recover in between each one.
The purpose is to build stamina, improve pace and to have some variety because running the same course and distance day afer day can get very boring. But it's a schedule which you can adapt all sorts of ways to suit yourself.
It needs commitment but not as much as the daily run which you have been considering. Just four a week, done properly, will set you up nicely. I would expect you to be feeling pretty good after 2-3 months. Good luck.