That really is a great question, and there isn't a great answer.
Your example of seeing oil rings could come down to the type of oil, how fast a given ball absorbs it, and even meteorological factors (temperature, humidity, etc) and isn't necessarily an example of HOW MUCH oil there is on the lane.
For me, it just comes down to bowling as many places as I can. I've bowled leagues in seven or eight different centers, and tournaments countless others. That's a good way to get to know "oh yeah, this is what heavy oil is.
Another example is practice in the summer. Most places oil their lanes less often in the summer since there are fewer leagues, and the heat makes what oil they do have go away quickly. That's a great way to find out "oh this is dry!"
But most house shots are dry outside and heavy inside. Even though you'll read all over the internet "I can't use heavy oil balls, my house doesn't use enough oil" you can interpret that as, "I refuse to move inside of 10 and am constantly bowling in the dry part of the lane."
On a house shot, you can usually use just about whatever you want if you're willing to adjust to play the angle that's suitable for that ball. And then set your arsenal up around that ball.
Nowadays, I open bowl practice and go to Nationals every year.
USBC Open personal bests: 226/602/1690
USBC Open career average: 174.66 (45 Games)
See you in Reno 2020!