Posted this at TOMB in answer to a 16 y.o.’s question:
There’ll be as many opinions as posters here, but FWIW, and it’s just mine, I’ll reco to you what I have to local friends.
Cassette recorders are cool and all & I’ve had and still have my share but they are lo-fi and now old and prone to breaking down, and tapes are not super easy to get. There are ways to re-create that lo-fi sound when using newer, digital recorders, with a little research, if that’s really what you want.
Me, I reco a inexpensive digital recorder. If it’s just one-take demo’s, I reco you get something like the Zoom H2, but since you seem to want to multi-track, I’d look for a SD card-based system.
FWIW, I use a Zoom R16 frequently to record drums (load into computer and overdub the rest), and it’s sturdy, easy, and sounds good, can be had for under US$250 used, has phantom power and effects, including compressors and EQ in the digital realm. I believe there are 4-track and 8-track and 16-track versions from various manufacturers, some that can be found even cheaper. They all seem to interface with computers through USB as well as the data cards; that is good because you can dump or mix your tracks and edit, etc. with cheap or even free software (the Zoom R16 comes with Cakewalk LE, I believe), which increases your options and odds of getting good-sounding results, and allows you to burn CD’s (for your parents and other dinosaurs) and post on-line, etc., and you even needn’t necessarily buy a soundcard.
Mic-wise, I reco the Shure 58 – pop the ball off and it sounds quite close to a ’57, and those are bog-standard mic’s, which makes ’em a good learning tool. But there’s usually usable and cheaper mic’s around – I started using Digital Reference 57 clones on overheads and was happy for a while. After that, while you might get longer term good use out of another 57-type, there’s nothing wrong and a lot good with learning about condensors, and there are tons of cheap ones out there that are certainly usable, from MXL, CAD, MCA, etc. I strongly reco you buy used – just pay attention to buyer info if you are on Ebay. (98% or lower, don’t risk it, do research prices, pay attention to condition and returns policy, etc.)
Two more tips to get ya started:
1. do try and do some sound treatment, even if that means using pillows and couches and closets and bookshelves and blankets – there’s lots of info on line on the hows/whys but the bottom line is you’ll maximize your results;
2. do try and use as many mix-monitoring approaches as possible, not just headphones – compare the home stereo, bookshelf stereo, car stereo, I-pod, etc.
Welcome to the world of my favorite waste of effort and time and money! 
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vlayman; THD; blog; TFP
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