If Jay Noone files a federal lawsuit against the Town of Palmer, MA (and especially one against their lawyer), I predict that he will be sanctioned by the federal court for filing a frivolous case. I don't think that Jay will even have the chance to present the case to a jury as it will be dismissed at summary judgement by the judge. This will happen because his case is grounded in legal arguments (decided by judge) rather than facts (decided by jury).
I completely understand the philosophical argument behind tax-sales being tantamount to theft. In the reality that we live tax-sales are considered by courts to be legitimate uses of government power. Challenges to long lines of precedent (like some federal income tax arguments) are considered frivolous by courts and can get people in significant trouble. Like it or not, it is the reality in which we live.
I really think Jay should talk to a lawyer before he does these things independently.