Hi I have one simple question that searching google hasn't really found me a good enough answer. Can having too many directory links harm your sites listing in google?
Only if by some miracle you managed to get them all too quickly... but that is unlikely given the slow nature or free submissions combined with needing a large budget for all the paid directories. So the answer is no, it is extremely unlikely that it would have an adverse effect on your site. Just IMO of course
If the directories are from different IPs, it will help inrease your pagerank. But if many directories are from the same IP (many people run many directories in the same hosting), then it's will not help too much for you.