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