Terrific article, Rick.
The most FUN I had playing baseball was in a sandlot environment, usually a school ball field during off hours. But there were frustrations.
First, sometimes you couldn't find enough players at the moment even to play over-the-line. In most cases there were compromises because of the lack of six players, much less eighteen, and often you were pitching to your own team to make it work.
Second, sometimes the condition of the field made it difficult to play meaningful baseball.
Third, sometimes basic equipment was lacking. Did you ever, like me, arrange to meet at the ballfield only to discover there were six players but only two gloves, and sometimes nobody brought a bat? And pity the guy "catching" without a mask. There were a TON of passed balls.
Fourth, it could be frustrating when some guys who showed up literally could not play. If you were on the team stuck with them, you were hosed.
Fifth, sometimes the appointed hour for the meetup was uncertain, and you were hanging around the ballfield for a couple of hours waiting for guys who might never show up.
Sixth, sometimes you had some guys who simply could not compromise on a ruling, be it safe/out, ball/strike, fair/foul, etc. The game devolved into arguing rather than playing.
That said, WE HAD A BALL DOING IT.
As a young teenager my favorite was impromptu games were held in our family' back half-acre, which was nothing but weeds and large clods of dirt, and it had a significant uphill slope. Predictable bounces simply did not exist. Bases were hats, or jackets, or towels, or garbage can lids, or shoes, or WHATEVER. And often you had to parcel out really little kids (and GIRLS!) onto the teams. Sometimes making the teams took longer than the game itself.
BUT WE HAD A BALL DOING IT!
In my later teens and early twenties it got to where my favorite baseball times were playing over-the-line with friends who could mostly play.