I have a 289 2b and am about to pull the engine, change all the gaskets, upgrade the cam with a cam kit that includes a new timing chain, springs, intake, carb and re-work the heads to match.  i am looking for some advise on what to look for and in a machine shop, what questions to ask and what i should have done.  Three angle job, etc.  I do not mind spending a little more money to upgrade different parts but do not want to spend it if i will not get the advantage of it.  What should the cost be about?  Would it be more  cost effective to just buy new  heads?  Thanks for the help.  

Ask around and find a machine shop that works on Ford heads.  To be fair when comparing rebuilding the originals with replacing them, you should probably consider having hardened seats installed in the heads for the exhaust valves.  In the 60s a lead compound was added to gasoline to increase octane and lubricate the valve faces.  There has been lots of discussion and things written about whether this is necessary or not.  If you are going to drive it a lot and drive it hard, maybe this is a good idea.  I don't know how good the lead substitute additives are.  It will take a lot of machine work to get the original heads to do what the aftermarket ones will do right out of the box.  The machine shop should give you a price and you can compare the costs.  If you are sticking with the 2V carb, keep the original heads and just have the machine shop do what is necessary to keep you going for another 100K miles.  Aftermarket heads need a 4V carb, cam, and a good exhaust system to work properly.