Did Israel ever keep the Year Of Jubilee?
As far as I can tell, the answer would be no. In fact, reading through the section concerning it, it almost seems more like a prophecy than a statute. I think it is insightful to God's thoughts on society:
1) Agricultural basis. When people buy property so much as buying harvests. Since all the land goes back to the original owners every 50 years, a person is buying profits from harvests, not permanant farm land.
2) Middle Class. God avoids perpetual poverty and extreme excess by balancing everything. If your family has it either really good or really bad for a couple decades, the debts are erased and land returned twice a century.
3) Complete Trust in God. Being willing to turn back peoples land, cancel debts, and not plant food all takes faith. My guess is ancient Israel did not ever do the Jubilee because of a lack of faith. Modern Israel is not too different.
Can't wait to try this rule out in the Kingdom!

Sometimes I tell my students that my job is to get them in trouble. For example, this week many students were pulled out of class for choir practice. The choir picked one block to have all the girls, and another to have all the boys. Finally, she had one practice where she had the girls wait to sing with the boys to have everyone together. So the girls were coming to class about 10 or 15 minutes late. I had four from my class and all of them made it back on time which made my life a bit easier. Then another girl needed to go to the bathroom, and made it back in about 30 seconds. When I asked why she was so fast (although I appreciate them hurrying) she said there was a line. Well that caught me as a bit odd, so I told the office that they might want to check on why there would be a 'line' of girls in the bathroom in the middle of class. Sure enough, three girls had decided since they had missed the first 15 minutes, they might as well wait the last 30 minutes out of class (science class as it turns out). And amazingly, all three were smart, typically well behaved girls. Now maybe they have me snowed and are not good girls, but I think there is another issue.
The science teacher is known for being very VERY strict. While there are times that I envy her abilities as a classroom manager (my classroom probably looks like organized chaos compared to hers), her tough stance on discipline almost creates as much rebellion as it squelches. Ironically, her rigidness and toughness means that many of the students who tend to run the wrong way in classes where they have more rope (like mine) don't give her issues, because they have no rope! On the other hand, some students who are mature enough to make good decisions end up making bad decisions just because they are rebelling against the rigidness of class. If I could have picked three students who give me headaches everyday, these three would not have been on the list (unless the list included all of my students).
Anyway, it's an interesting lesson to me that it is a very difficult balance to have the appropriate amount of rigidness and looseness. I probably err on the side of looseness, which means I lose some battles, but I also now see that erring on the side of rigidness also losses some different battles.
Being a teacher is fun because I get to keep learning!