the condition will be reflected in the price - the issue of how much it matters to you is up to personal preference. i'm very particular about condition, so if i saw a beat up copy of a book for $100 that would sell for $400 in fine condition, i wouldn't buy it, since i'd inevitably end up convincing myself to spend $400 on the fine condition copy down the road. if you don't mind the rip on the cover and the price is right, i'd buy it. feel free to post books you're considering here so that the community can weigh in on them, too. that way you'll avoid paying too much, which is unfortunately easy to do when you're just starting out.
for women and ham on rye, i'd focus on finding a paperback first printing. the hardcover first printings are going to run you many hundreds of dollars, and the signed hardcover first of both will usually be over $1000. a paperback first of post office in fine condition will be at least $400-$500, since it was fairly limited (2000 copies), but you can find copies from time to time with a faded spine or foxing, and if you can stand the condition issues, it's a good way to have a book with a lot of history behind it. you also might want to look into paperback firsts of the early poetry collections - days run away, mockingbird, etc. they're really nicely done, fairly limited, and not too expensive (less than $100 on eBay if you're lucky).
another nice copy to look for is the second trade hardcover printing of women. not sure how much backstory you know, but the short version is that bukowski's publisher added a bunch of "edits" to the first printing of women, and buk made him reprint it with the original text restored. you can find the second trade hardcover for less than $200, and it's a really handsome book with a black corduroy spine. it isn't a true first, but it's a significant copy of one of bukowski's best novels. i got my copy from jeff maser a few years back.
last thing to watch for - buk's publisher put out broadside flyers of a lot of books, and they can be found for relatively cheap. the ham on rye broadside is especially nice. i don't know if there's one for women, but you can put together a nice collection of flyers if you watch for them on eBay.