New Build Questions - Coffee vs Kaby - Black Friday/Cyber Monday

I've got a few questions, any advice appreciated!

I have been holding off purchases for my first hackintosh as I've been doing more and more research and learning the ropes. Before I take the dive, I have a few questions: I have never consistently kept track of computer component prices so I was wondering if I can expect many good deals for computer components coming up for Black Friday and Cyber Monday?

I assume the i7 8800 will not be discounted at all since it isn't even in stock consistently... but the 7700 has been decreasing in price consistently in the past 2 months. I've been tracking a lot of items on CamelCamelCamel. Should I just go with the 7700K or buck up and get the 6 cores to make my machine a bit more future proof?

On a similar note: The 8700 is only compatible with Intel 300 Series Motherboard. Will the 7700 work with one of those motherboards so I can upgrade in the future if I choose? Or would I have to get a new motherboard and processor if I want to upgrade in the future?

Should I avoid local used components? I've kept an eye on Craigslist and there's been a few 7700's and graphics cards. Anything I should watch out for or should I just avoid all that and get new? I'd of course get compatible components by referencing build guides and TonyMac

For some background: I am new to PC building, but I know enough about computers that I'm confident in my ability, and I will learn as I go. I've had my MBP for 8 years (maxed out the RAM, and swapped the HDD and CD Drive with two SSDs to keep it workable up to now). I plan to use my new machine for a long time as well, and I will be doing a lot of CAD and 4k video editing with it. I already have 4 multi-day backpacking trips worth of 4K drone footage (~10 hours) that I'm dying to go through and I do CAD modeling for 3D printing and design work for wood and metal fabrication! My MBP can't handle the 4K videos and is really testing my patience with newer CAD software... :(

Thanks for any input.

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