I was in your shoes around this time last year
I'd had the bug for years (just kept telling myself not to do it). I'd been involved with MotoGP for a number of years, but it was a recent adventure biking project that finally pushed me over the edge.
Did my CBT in Nov last year and told myself right from the start that if I didn't feel safe during or after the days training I'd call it quits and walk away – I'm glad I didn't.
Got a 125 in January, fully intending to do the full test before the new one came in, but to be honest I'd never have been ready. Since Jan I've clocked up 2,700 miles both around town (traffic), and out on the open roads. I have to confess that I avoid the wet weather (mainly 'cause I just don't see the fun in it and I'm doing this for fun not purgatory), and I expect I'll be restricted to weekends only now the nights are closing in. Though I've been using the bike for my 50mile round-trip commute to work quite a bit.
Looking back I'd say there's no way I'd have been safe doing a CBT then a 5-day direct access. I can see how people hurt themselves going that route. Spending a year on a125 learning smoothness and correct road positioning and control has been well worth it in my opinion.
Having been a driver for nearly 2 decades what surprised me most i how much more your concentration levels rise on a bike, and how much more you see – it's certainly made me a better driver, though I know I still have a very long way to go regarding the bike.
I'll be on the 125 through the winter now (when weather permits) and into next spring, then I'm doing the full test. Not sure yet if it'll be direct access or if I'll do it on my own bike (which leads to the 2 year 33bhp restriction). Just got to do my theory test (crazy given I've held a car license for so many years, but still.)
On to your questions though:
1. Roads are terrible for bikers, full of pot holes, tar lines and broken surfaces (and that's just my street) – Honestly, they're not so bad – you've just got to know the limitations of the bike and ride within them. Oh, other road users a a bloody nightmare, but if you treat everyone around you like they're out to kill you, you'll probably get by.
2. I've got 3 gert-big locks and a rain cover to deal with, not to mention jacket, trousers, boots, gloves, helmet etc. to sort before the bike can go anywhere – all-told about 20 minutes effort. I can just grab the keys for the car and be moving inside 30 seconds so No… short journeys (to the shops etc) are more hassle than it's worth. I rarely go out or less than an hour at a time.
3. Tried leather but it felt too restrictive and I don't like the power ranger look anyway – no denying it offers good protection, I'm sure, but when you're starting out anything that's a distraction takes attention away from learning. I went with textiles – jacket and trousers zip together – and didn't skimp on quality (figuring if I didn't drop the bike it'll last me a long time, and if I did I wanted all the protection I could lay my hands on). Initially went with textile-based winter gloves as they seemed to fit better than leather for me, but by the summer realised they were too hot and ended up buying some nice kangaroo and carbon gloves – now I don't feel safe if I wear the old ones :? Get a good helmet, and try on as many as you can (visited Hein Gericke 3 times and can honestly say I tried every medium lid in the shop a dozen times or more – I now know why people say you have a shoei-shaped head or an Arai-shaped head or so on – they all fit that little bit different, when you find one that' right everything else feels all wrong (see comment re. distractions again).
4. There are hundreds of things you've missed, I'm sure – but I'm still learning so I'm that last person you should be asking
Everything I've put here is an account of my own experiences and nothing more. I just hope it helps to hear it from someone who's going through what you're considering. The new two-part test has got a lot of bad press, and the BMF are really laying into the DSA for it, can't see they're going to change it though.
5. Are you crazy considering a motorcycle??? YES, but then aren't we all a bit mad?
Seriously, give it a go. Who knows you may come to love it.
I don't consider mine to be a mid-life crisis either – I may be mid 30's, but as my wife keeps telling me I act just like a child