It would be simpler for sure, but there's no way to be sure of the future (i.e., at the financing) relationship between share price and overall valuation. This

It would be simpler for sure, but there's no way to be sure of the future (i.e., at the financing) relationship between share price and overall valuation. This is because, of course, the noteholders can't know how many shares will be outstanding at that point. If you wanted to translate a $5MM cap, for example, into the equivalent price per share, you need to know how many shares are involved. The noteholders don't know what that number will be when they enter into the notes.