At my stage of life (past retirement age, but working and earning full time until I drop) money isn't an issue, so I get pretty much whatever I want for my shop. OK, money IS an issue when it comes to space. I can't afford to move, and there's no way to expand my 18 x 18 garage shop on this downtown property. As a result my space limits my purchases and I can't really test the "money is no object" situation to its fullest. So, I suppose a better description is that I have way more money than time.
I chose a new Bridgeport style mill and a Hardinge clone by Sharp, and I've not regretted either for any reason - both have built in VFD, rotary phase conversion and DRO. Most of my lathe work fits in collets, and I don't work on big stuff with the mill, so they are both beefy enough for me to get really good accuracy and finish. Once I saw the Hardinge style single point threading in action I was hooked. A separate drive motor for the carriage means I can really dial in the finish. That pair of machines cost more than a nice new car, so I simply put off the car purchase for a few years - no big deal. By now, I've more than doubled the cost of that gear in the tooling I pick up as it seems useful.
I don't see CNC in my future, mostly because of the kind of work I do. I'm really a hand-craft kind of guy, and I can relate to the feel of cranks and handles, but at this point, not to CAD or CAM.