The idea of the Free State Project is not to get a two senators out of 100, arguably we already have at least two conservatives in the Senate. The idea is to use elections to move one state's internal policies towards a simpler, smaller and lower cost form of government. This would be more in line with what many believe the founders intended and the Constitution calls for.
Thus the focus would be on the elimination of unneeded state laws, regulations, bureacrats, programs, fees and taxes.
Things might get interesting when the State government began asserting itself under the 10th Ammendment.
"The powers not delegated to the United States by the Constitution, nor prohibited by it to the States, are reserved to the States respectively, or to the people."
This ammendment, tortured Supreme Court interpretations of the commerce clause notwithstanding, is violated every day by the federal govenment. Only a State has the standing to challenge this. Wyoming has already told Federal alphabet soup 'law enforcement' agencies they may only operate with the knowledge and agreement of the local sheriff.
I don't think an early emphasis will be on ending all drug and prostitution laws. I think ending welfare is a much more likely first action, and gun control. Most gun laws are federal, and the feds are quite willing to enforce them for cities that don't want to do it themselves. (As cases in Santa Cruz and elsewhere have shown.) 