I'm proficient with bicycles growing up, except that I've broken 5-6 of them. Either the break starts malfunctioning and frictions with the wheel even when i'm not pressing, the pedal falls off, the derailleur gets caught into the chain. These were all bikes given to me growing up so I just tossed them when they broke. Frankly, I'm tired of extra parts just causing trouble so the simplistic idea of a fixie appealed to me.

I'm looking for a bike that could last me in the long term and I've never experienced with fixies or single-speed but the BMX i once had and got stolen. I don't have a big commute to do on bike beside going through a hill. A multispeed bike would overcome this problem easily, however, they've caused me far too much problem in the past. Assuming the little hill isn't too much trouble for a single speed bikes??-- I'm considering a fixie with a hub that can switch if I ever don't like it, or a single speed?? I live in Canada, so I can't simply just order the kilo TT. That'd be cool. There's tons of fixies selling around, even local brand fixies also. I don't want to pay for something that isn't worth it's price y'no? What should I be paying for the average craigslist kind of fixie?? I think this'd be the easiest way to narrow down my choices. Oh, and is there anything I do about knowing the reliability of the bike?? I REALLY do not want another one to break on me..

Buy one.
Ride it.
You'll either love it and buy a better one, or you'll hate it and sell it so you can buy a bike with gears.

BTW, your past issues have more to do with the quality of the bikes and the efficiency of your maintenance than anything else. Any half decent bike that is looked after will give years of service.

SS/FG has its place and there's nothing wrong with having a SS/FG plus a geared bike (I do so it must be okay right?). They're also cheaper to buy and you'll have something to ride while sussing out (and saving for) the geared offerings.

Well I was looking to just have ONE bicycle. I don't intend to make bicycles my hobby. 300-400$~ for a fixie that's kind of no-one-knows-the-brand sounds reasonable??

You could just walk. Shoes are low maintenance. Part of the problem you are having with bikes is probably related to the amount of money you are willing to spend and how you are spending it. With your budget you are much better off trying to buy something decent from craigslist. Don't try to buy a bike from Canadian Tire. Fixed gear or not a big box store bike will be a pain to maintain.

edit: Does purefix ship to Canada?

Many bike shops have used bikes. Some have used single speeds. If you could add about $100 to that $400, you could get a really nice brand new single speed. Good Luck!

If you don't take care of your bike and do regular maintenance things will happen like your brakes rubbing, pedals falling off, derailleurs not shifting right, chains falling off. These are all problems with you, not with the bikes. I'm sure if you put a little money and/or elbow grease into your previous 5-6 bikes you would still have them

Shame on anyone who's reaction to the brake rubbing is to throw the bike away. You can fix that problem in under a minute for no money.

OP I don't think fixed or single speed is for you. Bikes aren't for you. That's okay, people have different talents. I know I'll never be good at getting my head stuck in fences.

Pedals that aren't properly tightened will fall off;
regardless if the bike is geared or fixed. Are there
bike cooperatives/kitchens in your area. They can
help you build a bike. You'll learn about
maintenance and save money at the same time.

No. Fixed is not for you.

youre getting made fun of because you put zero effort into maintaining the machine that so graciously supports your weight and carries you to any destination, for free, that you want it to. if you dont maintain a car, it breaks down. learn some basic mechanic skills and save your hard earned money. sure ssfg is for anyone, but they have to be willing to work for it.

Try it. Seriously, if you give up now, you'll never know. Just make sure you have your mobile phone with you so you can post on here with the results (preferably a selfie)

You know, it's hard to ride any bike through a hill. You know with all those trees, not to mention rocks and dirt.

Go for it, but remember a ss/fg is still something with moving parts that requires maintenance.