This would make retirement harder and harder, but also worth the effort. And we won't see a huge group of 1-3 retirements and then a small group of 30 retirements or more.
A "Harder" system means you have to spend more time to get heirlooms. This means that the people who spend the most time playing, will become even more rewarded for their heirlooms than they are now. It will only widen the gap between people who play a lot and people who don't as more time will be spent on each following gen.
If someone plays for 1000 hours on the old system and reaches gen 31 thus having 10 triple heirloomed items. they're most likely only going to be able to use a maximum of 4 of those at a time. 4x3=12, 12+1 = you'd have to be gen 13 to be on even ground with them. It's about 500 hours with the old system to reach gen 13.
With the new system or even the one you propose, there are always going to be people with a ridiculous amount of heirlooms and generations, it just makes it harder for everyone else to be on equal footing. to get to gen 13 with the new system, you're looking at about 750 hours.