Forum Moderators: martinibuster
First, automated e-mail link requests won't get you banned from search engines, but they WILL annoy webmasters. Not only will the latter delete your link request with barely a glance, but they might report you to spam abuse agences, your web host, etc. Most software lets you write an individualized request, which should greatly reduce this risk if you are diligent.
Second, annoyance with spammy link requests and overaggressive spiders has led some sites to ban user agents identified with link-management programs. This won't affect many sites, but well-managed, higher quality sites are probably more likely to implement bot-banning measures.
Third, if your software conducts automated searches, Google or others could penalize your IP. It's possible, though very unlikely, that a domain could be penalized for excessive searches; they would have to have a way to tie the searches back to your domain (e.g., searching from the same IP address, etc.) Be aware that automated searches are a TOS violation unless done on Google's terms.
Fourth, auto-generated directories have been problematic in the past and have led to blanket penalties. While this may or may not be true right now, if you autogenerate a directory, I'd go through every line of code to be sure there are no software footprints left AND also be sure that the directory was of reasonable quality. Hideous collections of random links should be avoided, to say the least.
There has been some discussion lately that some directories may have lost their PR, and I suppose this could apply to link directories regardless of quality or method of creation. How some directories might be singled out while others survive intact isn't clear yet.
So... while there's no automatic hammer waiting to drop as soon as you boot up your link software, you'll have to be vigilant to avoid the potential pitfalls. You'll have to weigh the productivity benefits against the risks and costs. Small link campaigns can probably be run easily from a spreadsheet or database. Bigger ones may benefit from automating some parts.