Re: Getting around a County Sheriff
1) Be careful about a lot of the replies you are getting here. Like you, I am based in colorado. Recognize that these folks are coming from other places and some of them may be able to ask a city chief, etc but that does not apply in Colorado. In CO, by state statute the Sheriff of your county is the Chief LEO for that county. He (and his agency) is the one that should complete this process for you in this state.
You may find this useful as it is specific to CO:
http://www.douglasturner.com/2010/03/15/faqs-about-colorado-nfa-trusts/
2) Do you have reason to suspect the Sheriff will not sign? If you are in CSPrings, then yeah you are screwed. Other than that, it varies widely county to county.
3) Its hard to find a local attorney who will tackle a trust for you. The ATF has given grief (and recieved some) to/from some of the "known" gun friendly attorneys who do this kind of stuff so do not be surprised if you have to check with a few before you find one who will do it for you.
4) Quicken is a way to go but remember that at the end of the day if you go a trust, you need to make sure someone who is more legally versed than you (preferably a licensed attorney) ensures the validity of the trust.
Contrary to what some of the posters above have asserted, the examiners will not validate your trust in the respect of ensuring it "holds water" and will "hold up under challenge". More of what they are looking for is "is this really a trust" and "is someone trying to dodge the law here who shouldnt really have this". There is a BIG difference between the two types of review.
And -- word at two local gun clubs i frequent is that the ATF is doing a lot more sabre rattling about trusts so you need to just make sure you are protecting yourself by doing it right and getting the right people involved.
5) LLC IS an option but if you dont understand what an LLC is or its tax implications, etc, then do not confuse yourself by going down that road.