I had used cars most of my life up until I was in my late 20's. Up until I was about 24, My most expensive car was under 1k. I paid for all but one of them myself. My father had helped me out one time. The one thing that I didn't care for about cheap cars was that there was always something wrong. Even when I had my reliable 92 Honda Accord.
I know nothing about cars mechanically. I tried to learn but it did not interest me at all. I found that I was either always worried about my car starting, always in the shop, always looking for a ride when my car was in the shop, always nervous of breaking down on any semi-long trip (I did break down many times), and always laying out A LOT of money for repairs. It seemed like every time I went to a mechanic, something new broke. I'm sure most people know that feeling.
When I got a real "secure" job, I decided that I'd rather pay a little more money for something new, so I wouldn't have to worry about all those problems and wouldn't fear missing days at my new job. I decided to lease a ford focus. It was about $200 a month and probably the best $200 per month I ever spent. Very reliable, great on gas, affordable, I could take long trips again with now worries and pretty much all my other worries went away.
I feel like the $2400 per year in monthly payments probably equaled the amount I paid in repairs each year and time taken off from work to get my car fixed. Even if the repairs were a lot less, the peace of mind was WELL worth it.
Since then, I have never bought another car again. Always been leasing. I love the feeling of going out to you car in the middle of the winter and knowing its going to start. I also love the feeling of taking a long trip in the middle of the summer and not having to worry about over heating. Not having to worry about missing work. Not having to worry about going to a mechanic. Not having to worry about finding rides. Etc......
You don't have to lease an expensive. There are plenty of cheap leases out there for under $200. Some of them are really nice, safe cars. Just know your limits. If your making 50k a year, don't get a Lexus. If your making 100k, Don't buy a BMW. Live within your means. And, if for some reason, you decided you made a mistake and can't afford your payment, you always have swap-a-lease. I have friends that used it and have gotten some good reviews.
In the end, it all depends on what you prefer. If you feel you can save more buying a cheap car, then go for it. If you want the security of a new car, go for a cheap lease.