If you are worried about your son getting discouraged, the new premium features will let you create any kind of problem set you want. For example, you can create a set of problems with ratings under 1000 standard. Then when your son finishes all of those, make a problem set for 1000 to 1100. Etc. Or make a problem set with Mate in One. After finishing that, your son can do Mate in Two, etc. These are all unrated, of course.
I am not worried about him getting discouraged as I am right there with him to encourage him. But, now that the rating of the problem is hidden until you attempt it, I end up solving it in my head and then deciding if I want him to concentrate on it a while based on my best guess of how difficult it is. When the problem rating was displayed I would just skip until a sufficiently easy problem was on the screen for him to attempt.
The premium feature you are describing would be a step in the right direction, though I think more reasonable problem selection could be implemented (and fortunately the idea seems well received by Richard).
I'm not sure I understand the reasoning behind having a narrow rating range of problems served to weaker players, and a wider rating range to strong players. My thought is that the difference between an 1100 problem and a 1300 problem is not as much as the difference between a 2100 problem and a 2300 problem. 2300 problems are almost impossible for me to get right, but 2100 problems I have reasonable chance. The range I get now seems wide enough. I wouldn't want it to be a lot wider.
You are a considerably more skilled player than I am, but respectfully the difference between a 2100 and a 2300 problem is theoretically much less than the difference between an 1100 and a 1300 problem. The former represents a problem that is 9.5% more difficult ((2300-2100)/2100) whereas the latter represents a problem that is 18% more difficult ((1300-1100)/1100).
You have probably not been a beginner for a very long time, so it is easy to lose touch with what it is like to start playing a game as complicated as chess. I coach a scholastic chess club in WA State. I get kids that are total beginners all the time and I get to see them struggle from learning to just move the pieces, to finding hung pieces, to starting to recognize basic tactics, until finally they are able to start maneuvering their opponents into tactically advantageous situations. Each of these steps is huge in their development.
Taking a student who is at the stage where they can really only manage to recognize very basic situations like hung pieces or back-rank checkmates (ie, someone in the U800 range) and giving them mate in 2 exercises rated over 1300 isn't going to help them develop. They need easier puzzles until they are ready for more difficult challenges. When they are ready, their rating will increase and they will start getting gradually more challenging puzzles.
I am not advocating widening the range for more skilled players. When I said 'wider' with regard to that, I really just meant wider than for the lesser skilled players. The range for those players is something that can be adjusted over time as deemed necessary, but it has a large player base to provide solid feedback. Lesser skilled players, who are just developing their talents, are not going to get that kind of representation. It would still be nice to take their needs into account when designing the site as they are exactly who you want to attract. No other site caters to them at all. If you can get them early and keep them happy and engaged, then you have a long-term customer.