we have a 12 inch Rayco chipper and 12.5 ton crane.and my best buddy has an mfa in furniture design.
Your best buddy's MFA will not help you with the sawmill work, IMO. Just because he knows how to design furniture doesn't mean he knows about sawing timber up properly. There is an art to the sawmill, especially if you want to get the quality product out of it.
will the crane help me rotate logs as well as hydraulics and can a human cut straight lines on a mill or should we look into automated
Yes, the crane will help, but those cranes are slow to reposition a log. This is the very reason I mention it. I use an 8,000# forklift, it is quicker than those large cranes, but you need to use slings to wrap the log, cinch them low on one side and lift the crane so that the log will rotate onto another side. This takes a LOT of time when your working alone as I often do. If you have a 2nd set of hands to attach and position the slings, as well as spotting for you as the log rotates, that will go a long way. This is at the price of having a 2nd body to help you.
If you cut the logs shorter, it's easier rotate them with a cant hook, but you will need to cut more sections. It's a tradeoff IMO.
Chipper will help to get rid of the waste, for certain.
You didn't mention a debarker, could be a valuable little piece of equipment. If you don't use a debarker your blades will go dull way faster, so it's very handy to have. Even if you remove all the bark from the logs, which I do, there is still a lot of dirt and other cruft left on the actual log itself. I try to clean the log off best I can with brooms and such, but it sticks on the log and doesn't like to come off easily. All of that dulls the teeth. Having a sharpener and setter is very handy, they are not cheap either. If you saw through the bark, you will dull your blades in a few cuts. This is more so with certain species, like cedar which has a lot of silica in it. That is murder on blades.
If you really want to talk about work, quarter sawing requires more work than any other milling. You need to quarter the log up pretty much and rotate it for each cut, and the pieces continue to get narrower as you cut each quarter. There are ways to try and maximize by cutting the vertical grain out of the log, but in the end all of this takes time. And that is the killer, time, time, time...everything takes time. Turning a log takes time, stacking lumber takes time, letting it dry takes time, etc...
Yes, it can be done and people learn how and sawmill all the time. It is honest and hard work, but so is a tree service company, as you must very well know. As I have said before, I would rather be sitting on some nice quality lumber than a bunch of cords of firewood, but you need to realize what it takes to make that quality lumber, because it takes time...and as they say, time is money...