The probe/tool offset setter is super valuable to me and i had to get the IPS in order to use the probe. Other than that I never use IPS.
I bought the hard drive and extra memory and never use them (even huge files run off the USB) even though I do a lot of 3d contours.
I didnt get HSM and it was a mistake. HSM isn't really the correct name for the feature. Anything that isn't a long straight line goes faster with HSM and the surface finish is better. My impression is that if HSM isnt' on that the control doesnt do any look ahead, which results in a lot of stuttering in movements.
I have BT, order all my tooling online, and dont regret the choice. I have the umbrella but would be happier with the side mount if I could go back in time. Rigid tapping is a must as is setting spindle orientation to make rigid tapping repeatable.
I use Solidworks for CAD and HSMWorks for CAM. Solidworks is well known, so I don't have much to add. HSMWorks is awesome, both as software and in terms of the support.
The memory/hard drive/USB is straight-forward. If you want to edit a program, it has to fit in RAM. I always edit on the system that has my CAM software (the Windows based NC editors are a gazillion times better than trying to edit on your Haas), but I almost never edit the output of HSMWorks because it is already doing what I want it to do. I run my programs directly off of a USB drive which costs about 1,000 times less than buying storage from Haas (16 GB USB drive is $18 USD, VF-2 750 MB option is $1,595 USD, so Haas is actually 1,777 times as expensive now).
I think i should have gone with a faster spindle and through spindle coolant, but those are the kind of features that might have hidden negatives so you dont want to listen to my wishful thinking on those unless someone who has them says they are straight-forward improvements.
Overall have I been happy with my purchase of a Haas? Absolutely.
As far as tooling, i have been moving almost exclusively to shrink fit. I can't remember the last time I used an end mill holder. I buy solid carbide cutting tools from Lakeshore Carbide with either Altin (for steel) or ZrN (for aluminum) coatings, and will occasionally buy brand name tools that cost 3X as much that last 1/2 as long just to remind myself what it feels like to waste money.
Hopefully this is helpful.