it all depends on what your needs are boat requirement wise. insurance depends again on your requirements.  if your fishing big water, a larger boat. if your fishing tourney's then your policy must be able to cover that.  there's no way to offer suggestions untill you post what your hoping/wanting to do.

Rule of thumb get the best rig you can afford easily.  This could be a few thousand bucks to the full "Monte" pro style super rig.  BUT if you new to boating and fishing boats in particular I'd stick to something easy to learn on.  Trails and backs easy.  Not to complicated to run and maintain.  The learning curve on a brand new expensive rig as a first boat can be expensive.

Another idea is try to fish with guys with different kinds of boats.  OR.....Go to the boat ramps at lakes you plan to fish and look at the boats putting in and taking out.  Ask the owners questions.  Most guys will talk your ear off about their rigs.

Matt: I sent you a PM

dale