Would you be okay with the Saints giving up pick 29 and future assets for Jeffrey Simmons?

He would be an Unrestricted Free Agent free agent next year.

Not just would the Saint "have to pay him" we would have to have to pay him more than anyone else was willing to pay.

Giving up the 29th pick would be foolish.

If he would sign with the saints next year, why not wait 1 year, sign him next year as a UFA instead of burning a 1st round pick to get him.

Because he doesn't help the team this season if you sign him next season. Sign him to a long term contract. Good players are always cheaper now than the next year.