It all depends on how much you'll be playing. If you're going to go play once a year or every few years at bachelor parties, a $99 investment isn't too bad. I had one of those starter generic sets and it worked fine when I went years between rounds.
3 summers ago, I was stuck in a small town with nothing but golfing to do, so I ended up going out 1-2 times per week. That September, I upgraded to a nice $299 or $399 Callaway Diablo Edge Iron set, at end of the seasons sales, that was specially designed for amateur golfers in mind, bought a used $45 Nike Dymo driver, and a few used Nike SQ hybrid's for about $30 each. Now I'm golfing once a week or every other week and it feel like a nice solid set.
Don't be crazy and buy a $800 set if you're not sure you'll go much, but buying a $99 set, then upgrading to a $200 set, then moving into the $300 set will cost you more in the long run because you can't sell used generic sets for anything.
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