The main things that deterred me from playing cRPG earlier were:
1. Upkeep as a poor newbie trying to get gear on my own
2. Large stat/skill point gaps
3. Heavy cav roflstomping (though this was 2-3 years ago, nowadays HA is more of an issue)
Upkeep's a bit tricky since giving a grace period would let trolls that have lots of cdkeys plated charger + steel shield spam through armory items.
I'd be more of a fan of having characters retire to/start from level 20(or some higher level), and moving the exp requirement forward than mucking with gen exp mechanics/retirement requirements, since it'd encourage players to retire more often in general while reducing the "holy crap I'm useless" stage of the game.
Going from this:
1          0
2   3,000
3   18,375
4   34,173   
5   50,502
6   67,503   
7   85,349
8   104,259
9   124,512
10   146,455
11   170,528   
12   197,286
13   227,425
14   261,825   
15   301,595
16   348,129   
17   403,188   
18   468,987   
19   548,319
20   644,701
21   762,569
22   907,507
23   1,086,553
24   1,308,577
25   1,584,752
26   1,929,158
27   2,359,534
28   2,898,233
29   3,573,418
30   4,420,577
31   8,735,843
To this:
20   0
21   250,000
22   510,000
23   775,000
24   1,075,000
25   1,484,752
26   1,929,158
27   2,359,534
28   2,898,233
29   3,573,418
30   4,420,577
31   8,735,843