Will he or you be the one to suffer if something goes wrong?
Who is going to be held to account if the plan results in deprivation rather than plenty?
What is the exit strategy for abolishing the system if it doesn't work?
Where is the guarantee that this exit plan will be followed?
With all due respect to Lew, I'd suggest a few more.
(A) Where is the unequivocal universally agreed definition of the problem? It is not enough to say, for example, "homelessness", or "poverty" or "campaign finance".
(B) Where is the evidence that this proposal is a timely solution to that problem. Government and Politicians are great a providing solution to problems that are on their way to being fixed already only to make things worse.
(C) Who is going to pay? How much? And, who will make up the difference between your estimate and reality? The answers are universally the taxpayer, too much, and are you kidding. Estimates of cost are usually off by orders of magnitude.