I started riding a 50 scooter back when I was a teen. i'm unco as, wanted a VT250 (bike) but found it scared the beeejebus outta me (arm reach was the problem) and ended up with a 250 scooter. I had the 50 for about a year before moving up.
Being unco, it meant I didn't have any licence, and as I couldn't get a car licence on a scooter, it forced me to get my bike licence. I sat my full on the 50 (automatic), I argued the point with the traffic cops' receptionist, and ended up with a full bike licence, unable to ride a bike. Funny as hell really. When, 20 or so years later, I started riding a bike on the road (had a few years' offroad experience by then), the first time a cop pulled me up he commented I should've known better as I'd had my licence forever. I had to mention the fact I'd only been riding a few months lol
Back to the subject at hand. The 50 scooter was light enough to pick up when I dropped it (often), the 250 I don't think I ever picked it up by myself (actually maybe once when in a bike park the whole lot toppled over, but who knows, too long ago).
It gave me confidence to start riding, was a pretty flat ride to work (very important with 50's) and saved me heaps in bus fares. I also occasionally rode it on the motorway (scarey as hell being that slow) but it had to be when it was almost empty and get off as quick as possible (about an extra half-one hour if I was avoiding it).
Basically, those are considerations: terrain, roads likely to be travelled and speed of cars passing you. A 50 is scarey slow.
If you're looking at buying from a shop, talk to them about what they can offer you for protective gear. It doesn't have to be the most expensive/fashionable, but needs to be comfortable and should be better than jeans/skirt/jandals/shoes. Make sure you get gloves, I know I ripped my hands open a time or two when I fell off hehehe.
I have no idea what modern scooters are like (I don't think they've really changed that much in around 25 years - especially the 50's), but at least you can usually get decent tyres now (believe me, I tried to find some but had no luck and that was often the reason I dumped it).
I'd be saying (oh, I am) if you're looking at a cheap scooter, you'll want to upgrade soon enough, if you're looking at more expensive, you need to look at bigger than 50. My MIL has a 125 chinese thing and is happy with that (okay, it's 2k to her work and not used much).
The other thing is, not sure how big the petrol tanks are these days, but I know when I worked about 20k from home, I had to fill up every 2nd-3rd day (PITA big time), but it was only a few litres.
Any questions, PM/email me (I don't often pop into here, as I don't ride scooters any more).
Hope that helps and not confuses the hell outta you.
Michelle
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