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A few noob questions

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I'm an old man (40) who runs a business and has a family. I have a few noob questions, a couple general and some more specific with what I want to build.

GENERAL:
1) I've been told that as long as I don't update the OS that everything should continue to work fine until things need to be updated. On the other hand, when I do need to update the OS, what are the problems that typically arrive. Are they software issues or do you need to buy new hardware. And if it's hardware issues, are there specific parts that usually aren't compatible any longer?

2) If you don't update your OS, how often do you usually need to work on a bug or fix.

SPECIFIC TO MY BUILD:
I think I'm different than most people in that I'm interested in having a decently powerful macintosh, but I don't need it for gaming or video production. I'm a digital marketer, so I do a fair amount of photoshop work, so my main goals for my machine are the following:
- graphics cards which supports two 4k monitors
- small as possible case (I'd like something super cool and don't mind spending more on it... maybe something wood?) -- but I do need a motherboard that has native wifi with pci slot or however that works out. other words, i need wifi
- 32 gb ram but upgradable to 64
- 2 TB sds hardrive... and if possible a slot for a separate hd mayabe ata but i don't know if this causes a problem for the small case

Most importantly, I'm a total beginner and ease of build and stability are very important to me.

Thx.
 
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If Santaur can afford one of those, add in a liquid CPU cooler to go the full 9 yards ! Get some help from an experienced custom loop person of course. Water and electronics don't mix.

Will certainly be a lot more interesting to look at rather than another square or rectangular black steel box on your desk.

TRS 2016-11-06 at 8.18.16 AM.jpg
 
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