Scraping map data

Ok so I'm an avid Pokemon player who uses maps to source data on quests and create optimised routes for my friends n dedicated followers I've attached screenshots of what I do. What I'm after is a way to automatically extract data from a map and have it sort it by quests and if possible to optimise the route using the shortest hamiltonian path (problem can be rewritten in such a way that we can solve it with tsp tools) for the quests im specifically after. I'd need this done for various maps and have been able to extract data for a few maps but not automatically and there is one map in particular I cannot get the source data for so there may be debugging needed. As quests change frequently the database or scripts would need to be able to source the new data from the maps and require very little upkeep from me bar occasionally checking and updating few minor changes etc. I know this may have been done successfully using R studio. so long as it's user friendly as I don't have advance knowledge of computer language I don't mind how it's done or what platform is used