FYI – for me, the repurchase rights risk boils down to one quote from Peter Thiel’s book Zero to One (our book summary here). I ask this single question over and over again when screening deals as it helps to filter out a lot of potential investments:
“The biggest secret of the venture capital is that the best investment in a successful fund equals or outperforms the entire rest of the fund combined. This implies two strange rules for VC. First only invest in the companies that have the potential to return the value of the entire fund. This leads to rule number two: Because rule number one is so restrictive, there can’t be any other rules.”
If the possibility of the business repurchasing early investors puts the above at risk (having a single investment outperform the rest of the fund combined), then I tend not to invest, or at least I do it for reasons beyond just potential financial gains (e.g. I really believe in the product or founder, want to see the product in the world or use it myself, etc.).