Slate roof strategy:
1. Learn everything you can: "The Slate Roof Bible" by Joe Jenkins is the mainstay of modern slate roofing techniques. He has also published magazines and video posts and everything he portrays is in such a transparent and helpful style that one feels confidence building.
2. Get material and be a sponge for information: for my wife and I, this amounted to buying slates for sale in the area, getting a feel for soundness, learning hands on what a used slate with life left in it looked and felt like, the behavior of driving copper vs stainless nails into dry vs green decking, learning about slate types and identifying them (slate roof bible in hand) and so on... I went to a local slate resaler "the durable group, dba durable slate" who buys and sells slate and paid for one of the managers to take me around their warehouse space and 13 acre slate yard in columbus ohio to show me new and used slate. For a few hundred bucks cash and a morning he gave me an education that I would have paid 10x that much for. He explained where they get the slates from, acquisition strategy and sources, personal experience with the types and in convincing me that a used slate was worth what they were charging he gave me all the parameters of how to buy good slate for cheap... At the time it just so happened that he had several thousand square of buckingham black coming in off a 100yr old structure( with another hundred years of life left in it) salvage job and cut me a hell of a deal to take 50sq... Then I made a deal on some colors to go with that and came up with a pattern and final amount of slates plus 10-15% in case of catastrophe so that matching and finding spares would not be an issue. Total price delivered 12k
3. Find a good contractor that works reasonably: my parents and others in their neighborhood had used an Amish family of roofers because of their care, never cutting corners and work ethic. Not cheap hourly, but holy smokes, they had 2 guys nailing to chalk lines and one guy dealing shingles like playing cards to them both while 2 more were bringing shingle packs to the roof. 15 min breaks and work from sunup to sundown. Literally.
They had estimated 10-15 working days to do my roof but in fact they did it in 7 which included doing the siding on the high dormers, all the aluminum work on the fascia and putting up the seamless gutters all the way around. Total bill about 12k even though they had estimated their labor at 25k! Who has even heard of that anymore? Additional $1000 for misc stuff.
I watched and helped a little, knowing that I was slowing them down and still paying them at their hourly rate just to further my education...

After all that education by book and practical, I have helped local friends out with slate repairs and have found it very satisfying, relatively easy, and rewarding. I have done some small slate jobs pro bono to build my skills and feel more confident than ever that I could take on bigger jobs on my list of projects...
I also keep my eye out for good deals in slate locally (auctions and estate sales) and have relationships with area Amish through my medical outreach (yes there are still young docs doing house calls in this day and age). They gather the slates from metal roofing jobs they do and sort them per my standards and sell them to me... So my next projects will also use slate and at around $100/square in high quality material who can beat that?
What's even better is that a slate hammer, punch/ cutter, and slate hook tool are a $250 budget if that even. Throw in a used heavy duty 12' brake for $1-2k and now you can do your own valley metal and ridge caps. Joseph Jenkins also runs a nice online shop where I purchase nails, copper sheet, etc with the prompt and honest approach you just don't even see anymore.
I have done well so far paying for knowledge from trades experts, and never expect free knowledge. The amount I saved by paying the slate yard guy alone for his info is just amazing time after time. I feel that slate and the craft of it dovetails with timberframing so well that they have already married in my head. I also go through life with a whole new appreciation for the century slate roofs and some of the fancy slate roofs that are out there.
Hope that helps even though I went on a bit there...