I actually was thinking about this the other day.
But it's not that bad to get a start on heRO anymore.
1. Do the
Brasilis Lost Puppies Quest and
Item of the Day Quest every day till you are 90+ and have hit some comfortable job level (50+ generally).
2. Once you hit 85+ on any character sign up for
WoE Rewards and try to earn yourself 60 points for the War Boots (Verit effect of 7% HP/SP).
3. If you cannot WoE, get to 89+ and start paying to join
Battlegrounds for 3k Zeny for your first 100 matches. You will earn WoE Rewards Points there. Since you're BG'ing, pick up any other rewards that interest you that you can select at the time. The amount of points needed now for rewards is MUCH smaller than it use to be.
4. If you got the zeny, and some time you can forgo doing some of the dungeon quests by completing the repeatable
Army Supply custom quest! Use this for unlocking Nameless or Mosco if you just absolutely hate doing those normal access quests.
5. Do the holiday quests if you can. You should do this on all characters for experience and the gears you can later sell. They also often offer the opportunity instead to pick up past gears of the same kind (Christmas Quest lets you pick up past Christmas gears for example). Use this to build an arsenal of items to help further assist you in getting levels and money.
6. Since you sound like you'll need zeny early on, farm places that give decent amounts of zeny + experience. This includes Moscovia Dungeon 3, Nameless Dungeon, and Rachel Sanctuary. You can also try your luck farming cards in Byalan 4 since someone always needs a Marc.
Anyway, best of luck to you if you decent to return to heRO! If you got other questions about playing here feel free to ask me here, via pm, or in game.