I personally would feel it as I go with getting the level 4 rogue, then going to get the level 8 ranger because that is the minimum between each. After that, I would either see what has helped your party more. I personally would suggest going for what you have dealt with more: Urban = Rogue, Wilderness = Ranger. If it is an even mix or more urban-based and social oriented campaign I would suggest getting Rogue to level 12. If there is a larges emphasis on the wilderness or dungeons than I would suggest going ranger to 12 and then once again seeing if you want to reach further. If you absolutely need the damage go for the 4 final levels in rogue, otherwise if you need that stealth and defense boost then get the ranger to 16 to finish it off. This is assuming that your campaign will reach level 20. If not, I suggest just thinking about total levels of 16 and just getting the ranger to level 12 with a level 4 rogue because that is just better all around for a 16 level max game. Also, as a small aside, how necessary is Acrobatics as I feel your Dexterity will be high enough already and you are not as focused on Intelligence so you can make both Investigation and Acrobatics similar in level with just changing the proficiency and negating this whole thing. Also, I think Investigation is more often used than Acrobatics in the long run as you will just be making Dexterity Saving Throws where Acrobatics would otherwise apply. The main difference is if you really want to be seeking out your own tricks instead of having to just survive. Hope this was comprehensive enough!
You seem to have it fairly well planned out and yeah when the game is not certain of how far it will go I myself judge with a few set ideas of the goal level: Level 5 for quick campaigns, Level 9 for regular campaigns, Level 11 for hopeful campaigns, Level 16 for long campaigns, Level 20 is epic and only occurs with serial groups.
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I personally would feel it as I go with getting the level 4 rogue, then going to get the level 8 ranger because that is the minimum between each. After that, I would either see what has helped your party more. I personally would suggest going for what you have dealt with more: Urban = Rogue, Wilderness = Ranger. If it is an even mix or more urban-based and social oriented campaign I would suggest getting Rogue to level 12. If there is a larges emphasis on the wilderness or dungeons than I would suggest going ranger to 12 and then once again seeing if you want to reach further. If you absolutely need the damage go for the 4 final levels in rogue, otherwise if you need that stealth and defense boost then get the ranger to 16 to finish it off. This is assuming that your campaign will reach level 20. If not, I suggest just thinking about total levels of 16 and just getting the ranger to level 12 with a level 4 rogue because that is just better all around for a 16 level max game. Also, as a small aside, how necessary is Acrobatics as I feel your Dexterity will be high enough already and you are not as focused on Intelligence so you can make both Investigation and Acrobatics similar in level with just changing the proficiency and negating this whole thing. Also, I think Investigation is more often used than Acrobatics in the long run as you will just be making Dexterity Saving Throws where Acrobatics would otherwise apply. The main difference is if you really want to be seeking out your own tricks instead of having to just survive. Hope this was comprehensive enough!
You seem to have it fairly well planned out and yeah when the game is not certain of how far it will go I myself judge with a few set ideas of the goal level: Level 5 for quick campaigns, Level 9 for regular campaigns, Level 11 for hopeful campaigns, Level 16 for long campaigns, Level 20 is epic and only occurs with serial groups.