The main challenge installing guy wires onto a tiled roof was how to make anchor points. I went to a local antenna supplier and they told me the usual method is with these long self tapping o-ring bolts. So that’s what I did, it was much easier than I expected.
I used a diamond hole saw from eBay to make 2 holes in the roof tiles, and made use of an existing satellite dish mast for the final mounting point. I used threaded rod to attach a tapped o ring (or whatever you call it) to the satellite mast. Using a wet finger I was able to mold silicon around the anchor bolts in the roof tiles.
From my understanding it’s better to be earthed than not… I tried running conduit through this cement path using only an angle grinder and a chisel. This would have taken waay too long. Ended up buying a jack-hammer from gumtree (cheaper than renting). The second earth wire is from a UBNT Ethernet protector in the roof-space. This goes to a separate earth rod a small distance from the mast earth rod.