Aye dmac,
I do like your friend's plotting of his forebears travels through the generations. I suspect that they were shepherds and went to the Highlands as the estates were cleared of crofters/tenants to make way for the sheep.
Ironically, my wife is an Anderson from Tushielaw (landed gentry) and also an Anderson from from Badlieu/Carterhope (shepherd). Whilst I started my forestry in Strathglass in the early 1970's, so the first six places your friend's ancestors resided are familiar places. I'm happy to have a blether, if your friend thinks that I might have further information about his family or the general areas of their residence.
If I were to try and produce a similar map for my wifes family, UK, Africa, Caribbean, North and South American continents would be required. As FH does not have a mapping facility, may I suggest that you have a look at National Geographics, Mapmaker, application.
Link:
National_Geographic_Mapmaker
Sign in.
Use the base map, zoom in to the place you wish to pinpoint. If the scale is too large, I also have Google maps open on another tab, find the place on Google maps and then using landscape features place the point on the NG map.
Using the wee menu, number and colour the symbol, add the placename and a short description. Close the point menu.
Save the map.
I have produced a wee map of the two places where the shepherd was in the Scottish Borders, saved it and the then copied the link, so that you can view the map:
https://mapmaker.nationalgeographic.org ... 487b752daa
Open the link.
Move the map across to the UK, then zoom in to the two symbols.
Left click on the symbols and the name of the place and limited details appear.
Have a wee play around and see how you get on. It may do all you require.
Good health, Bill