I have often wondered about monetary position in my past lives too. During the First Crusades I was decked out as a knight, therefore my family had to have been extremely wealthy, probably close to what we may conceive as millionaires today. During the Siege of Jerusalem (1099AD) I had no urge to go looting like my fellow crusaders and this may be because I had knowledge that my family was wealthy so why should I pursue looting? I was the commanding officer of an Austrian foot regiment during the 7 Years War, and since commissions were usually purchased in that period, I may have been from a wealthy family. However, I have no real memory of wealth in any of my past lives, but that is may be due to me being quite young when I died -- I may have been from a wealthy family, but I never had a chance to explore what my wealth really meant or what I could do with it.
During WWI I was a junior officer in the British army, so I was probably middle class. Same can be said for serving in the US Air Corps in WWII, I was an average Joe pilot -- that could have been more skill than class privilege, but it still showed I had an education. During the late medieval period I was a sailor, so I was probably poor (I was barefoot, but then so were all sailors during the period). Just before the American Civil War I was a young clerk, so I was probably middle class, but I could have been from a wealthy family because I was educated -- I seem to recall my family was not poor but owned a house in a town or city. In the 1790s I lived in a small frontier village in the Ohio or Wisconsin region, so we were probably not rich, as we had a house and lived off the land to a large degree -- no telling if that was a rich or poor live style.
I have never had a drive toward gaining wealth so I doubt if wealth was of interest in my more recent past lives anymore than it is in my present life.
If I had to guess, I'd say I am middle road between being rich and poor. I have no memories of being destitute and poor. Perhaps we just never knew how poor we were? In my present life, I am from a middle class family, which is of the middle road.