I want to apply for 6 permits, but am only allowed to use 1 per month. I'm looking at the law and it says after the 90 days I may request an extension. So, it seems like it's not even guaranteed to get approved. Is it worth it to try for 6 or should I just get the 3 and repeat after 3 months. How was your town when it came time for requesting an extension?

Apply for six, then get three of them renewed.It's may issue, yes, however the "may issue" concept is on thin ice right now. The town should be cool about renewing them, most are. And if they don't, take it to court and you'll likely be the last guy they deny an extension to.

5 minutes. Rubber stamp the chief's signature and re-date.

get 6, if they deny the extension get three new ones...