I think the thing I dislike most in WT is that you enter a multiplayer game and you face planes completely out of your league because you have say a 1942 plane and face a 1950 jet. So are there any ways of selecting any multiplayer game where the planes match in time and place and maybe even theater?

I check on this about every six months or so.

The only thing closest to it is 'Enduring Confrontation Battles' in SB...
At least you will fly appropriate aircraft against an appropriate enemy.

Sometimes they have Enduring Confrontation Battles with Historical plane sets. Right after Christmas they had 3 of them running at the same time and it was amazing. Then they got rid of them and did the BR version.

Also look into playing sim Tank Battles, they have historical tank and plane settings most of the time.

True kestrel; but T-34's and Sturmoviks at the Normandy landings?