Let me just say, I know that this is a question that really only I can answer, but I thought it might be useful to collect my thoughts here, and get some of your opinions. We have to fill the internet up with something don't we? My Mac Pro still does everything I need, which is mostly hobby photography (Lightroom, Photoshop) intermittent gaming (nothing too demanding - Diablo 3 was the last game I played to death), general MS office and browsing etc, and I run a Windows VM on Parallels for some windows only work tools that I use when I'm working from home. It is a 4,1 hacked to the 5,1 firmware, upgraded with a 6 core X5650, 24GB RAM, GTX760 GPU, 960GB SSD in a SATA3 card, and a couple of larger internal SATA drives for bulk storage and backups. While performance is not too bad for my usage, it does occasionally feel sluggish, and while it it works with Sierra, and I expect High Sierra, it is unsupported, and misses out on some features like Apple Watch unlocking, and the new file system etc, It is a power hog, and at 8 years old I feel it is time for an update. I don't need a Mac Pro, and a new one is well over my budget anyway. I think a well spec'd quad core i5 or i7 would do what I need\want. The big sticking point for me is that I LOVE my Philips 40" 4K monitor....every time I sit down at it, I'm still blown away by having so much real estate. The options I am considering are: More upgrades for the Mac Pro. RX580, PCIe SSD, X5690 or similar faster CPU. But I don't think putting that sort of money into an 8 year old computer is a great investment. Top Spec 15" MacBook Pro. (NZ$4699) Gives me portability, but I have a 12.9 iPad Pro for that. I'd also have to spend about $500 for a TB3 dock of some kind, and get some form of external bulk storage. Expensive and 16GB RAM max. External GPU is an option to drive the 2nd screen in the future. 27" iMac. I'd either go with the top stock spec one (NZ$3849), or BTO with 512GB SSD (NZ$4189), and add 3rd party RAM. I'd still have to do something for external storage, although a simple USB drive for time machine would be sufficient if I went with the 2TB fusion drive option. The major drawback would be that I don't have room on my desk for a 27" and the 40" screen, so that would have to go. 21" BTO with i7, 16GB RAM, and 512SSD (NZ$3739) would just fit on my desk along side the 40". RAM isn't easily upgradable, so i'd be tempted to go with 32GB, which Apple charge a ridiculous price for. External GPU is an option to drive the 2nd screen in the future. I'm a bit worried that the built in display would make my 40" look bad Wait for an updated quad core, TB3 Mac Mini (don't laugh ) and add external GPU and storage. This would be ideal for me, but I will be surprised if it ever happens. Any thoughts\feedback appreciated.