Looking for the right path!

Thanks for all your advice. There is no set budget just like there is no set time limit. Should I take the machine shop a bare block and tell them to go over it or??? Can head work be done to open the valves to 2.02, without buying new heads or is the cost about the same? Not concerned about fuel economy, however I want to be rolling at 70mph and not 7k rpms. So I'm guessing highway gear ratio? I have 275s on the back now which fit nice. I more or less want a cruiser with some *** behind it.

Yes you can take them the block and have them clean and mag it , to start with.
To really get the ball rolling though...you need to figure out the rpm range and hp goal realistically attainable in that range with the gears you are chaining yourself to. kiddin.