It's about taste and eye appeal...
My focus for about 30 years had been postwar till I got my kids involved. To get them interested I had decided we would collect Pirate team sets from 1952-1973 (Clemente is the focus of my collection) which would include the early Topps sets through Clemente's last year of inclusion. After going to a bunch of card shows - my older son said "dad can we collect the old cigarette cards - they are really cool". I think my biggest hurdle was being very unfamiliar with all the nuances, pricing and variations in pre war - I didin't know the marketplace like I know post war. I used his request as an opportunity and quickly started learning. We now have a complete 33 Goudey Pirates set and are on our way with T206 (minus Wagner), T205, T207 and 1914-15 Cracker Jack. I have also decided that I really want to own a Ruth and Gehrigh card (maybe Cobb). I'm in no hurry, continue to watch the market and will pull the trigger when the time is right (right card for the right price).
Your question intimates that you don't put "new" money into cards as your example states you would sell off what you have for the potential new purchase? Is that true? If not, why not just save till you can buy the post war card (s) you speak of.
As others have mentioned numerous times - we should always collect what we enjoy! From your posts it sounds like you are enjoying post war right now a lot more than the thought of prewar.
Regarding grade - I echo the sentiment already expressed - eye appeal vs scarcity! In the case of certain rarities I am not very picky about condition. All of the cards you are speaking about are readily available any day of the week. I would hold out for one with great eye appeal - let the 3rd party grade be secondary - in the lower to mid grade ranges, Eye appeal varies widely!
Happy collecting
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