you should read "Chasing Points" about Gregory Howe,... ranking in 1000's and his journey to get points...
mentions some of things you're saying...
lucky draws
playing hurt seeds
searching for the most remote tourneys
etc....
Based on your post, I ordered this and just finished reading it last night -- a fun read. I started playing tennis about 10-11 yrs ago at age 36. I just kept laughing at myself...been a 3.5 my whole tennis life, and there have been days (lol...aka 'Monday')...i want to quit my job and devote myself to becoming 4.0 , follow the tour with my wife, and just become tennis gypsies and play all over the place. Then there are days I want to burn every piece of tennis equipment I own...HA!
Here's the thing I find interesting about tennis -- having taken up the sport later in life, I am what I am and I'm fine with it. Regarding the experiences and emotions I go thru each week as a middle-aged, ~20lb overweight, beer-drinking social/semi-competitive league and occasional tourney player...I found myself actually identifying with him as he described his emotions throughout his journey, even though the scale of the two of us is galaxies apart. That's the thing I've grow to really find fascinating about this sport -- it's something the lay-person can actually identify with at some level with those who are at the very top of the scale...
and I also enjoy the fact that as a player/spectator, the difference between the very top players and the 2000th best player is really razor-thin in the grand scheme of things...to me the 2000th-highest player is still awesome to watch, and there's always something to learn...
Anyway, he actually did it -- chose his path on his terms, spent his money/time chasing a goal. It was a very cool story, and I got to live vicariously thru him during the read...thanks for posting that.