But it really isn't that hard, and there is explicit logic in every step. If you are even remotely serious as an entrepreneur, you should be able to get 4 diamond endorsements with a handful of emails/phone calls - each of them with an expert in your industry who has an opportunity to publicly support you without spending a dime. That process encourages startups to network/pitch and is intended to create or strengthen bonds with helpful resources. These resources are not isolated to MA by the way.
Likewise, if you are even remotely serious about your startup, you should be able to get your friends/network to rate your company profile 5 stars very easily. This encourages you to promote your startup and seek support from your community. Easy stuff. No cost. Something you should be doing anyway.
Keep in mind, the endorsements and team ratings are worth only 10% of the judging score each. We had teams enter and win last year with zero endorsement points and zero ratings. (I don't recommend that as a strategy, but it's possible).
The application form itself is very basic: 10 questions, with short character limits. All standard stuff.