Valuation? Earn-out timeline? Return to investors? I know all of these are important to startups but what in your estimation are some of the biggest hurdles that make or break startup acquisitions?
Compatibility with your vision? Does 1+ 1= 3 or even 5? Personality mix? If you are going to stay with the acquired entity. These might be more important than any of the numbers.
After having had two exits / trade sales to listed companies with startups I co-founded I would say: Are you really willing to exchange your shares / entrepreneurial freedom for money / financial freedom and is it the perfect moment to do this step?