The book Where There’s A Will by Emily Chappell is a fantastic read that describes her journey through this race a few years ago. HIGHLY recommend checking it out.
The womens category should be reserved for cis women, and the mens category should be open to all. I know that won't please everyone, but it's better than outright banning a whole category of people.
I used to ride as my commute. My current job is remote, so I try to do a “fake commute” and ride first thing in the morning or immediately after work. Then I do a longer ride on the weekend; again, first thing in the morning (I sunburn easily, so earlier or later helps beat the worst of the Sun a bit)
It’s not “kind of” illegal, it’s illegal. And you’re not special.
In jurisdictions where it’s illegal, you have the added bonus of cars not expecting you to be doing something stupid like that. This puts you (and more importantly other people on the road) in greater danger.
Get a new bike. You won’t be able to tell what’s wrong with a used one and you might end up shelling out more than you need to if you find anything wrong with it.
Read up on bikes and listen to some podcasts. Bikeradar and Global Cycling Network have really good content that you can use to educate yourself on everything from frame materials to the drivetrain and tires and brakes.
Mountain bikes are heavier because they have shock absorption and fatter tires. Hybrid bikes have decent tires and can work great for commuting. Road bikes are generally for going fast. Do your research.
Don’t turn up your nose on the smaller brands. They usually get shit on by people on the internet because most people who love to talk about bikes are enthusiasts and have different needs. They might well have the perfect bike for your purposes.
Someone I know got a Linus Bike Dutchi 3i awhile back and honestly I wasn't really that stoked at first but -- I was wrong, it's pretty amazing. I've even thought about getting one. At first I thought they were just about the aesthetic but it's the real deal. Just a rock solid basic bike for running errands in town. If you don't mind, or prefer, single speed they have also have a barebones fixie/SS model for less $$.
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