I was sitting on my butt anyway so I went ahead and priced what I think is the absolute minimum . Price wise , for the minimal difference I see no need to even consider a 440 .
So the 770m it is .

The machine .
5 inch vice
Manual oiler
Power Draw bar
Stand , coolant tank, chip tray assembly.
Jog / shuttle controller
Fog buster coolant kit

Totals out at $12,000 and some change .

And I am giving the tool assistant package with the tool setter some serious thought @ $995

That would leave roughly $2000 to put towards work and tool holding .

Jwatte
You did a very good job of breaking it down .
My goal is to be right between your second and third level .
I feel the power draw bar is a must have , no exception .
I do want flood coolant in the future , but right now I'll have to live in a budget and settle for a mess and mist coolant for chip evacuation.
Preset tools sure seems like a big time saver to me as well .
I think the tool setter kit tormach offers fits inside my budget , at least I'm hoping it fits .

I never really gave the haas machines a lot of thought .
They are just beyond my budget .
The tormach I can pay for without stress or strain regardless if I ever make penny with it . And fix it if I break it .

While I could pay for a $40k machine with a lot of stress and life style cutbacks , if I ever crashed it and broke something I'd be out of business.