In general I am thrilled by the proposal and I think it’s an important milestone in aligning incentives congrats to everyone on arriving at this point!
To me, the weakest part of the proposal is using an OTC provider to do the buybacks.
An OTC buyback strategy lacks the transparency necessary for incentives to be aligned.
A concerning scenario would be that employees or investors are using the OTC buybacks to offload their tokens as they unlock. This would be concerning because it defeats the purpose of aligning incentives, with unlocks currently happening at a rate much higher than the planned buybacks.
Without the transparency of onchain buybacks, it would be difficult to disprove that this is happening.
I think I speak for a lot of token holders when I say that the transparency gained from hosting the buyback mechanism onchain is worth losing value in regards to execution price.
In addition, an onchain mechanism for buybacks would actually create incentives for more liquidity to exist onchain and may actually be a solution to the perceived problem.
I do think that @wildmolasses has some great ideas on how this could be executed in practice.