To be blunt, what do you bring to the table? Are you adding anything to the race that will make it worth the race director's trouble?
If you're going to whine before hand, race, request that you get your prize money as soon as you cross the finish and then leave, most RD's would just as soon you not show up. You certainly seem like this type based on your comments of the drawing. If you'd read the race brochure or paid attention before the race you would have found out when the drawing was.
However, if you're not rude and ask the race directors in advance and state your goals, etc, and maybe note you're going to work with the RD identifying some other top flight runners that also would be interested then you'll get some support. Don't expect free entry just because at some point in the past you ran "X" time.
Personally, I don't have much problem supporting young local runners that are truly talented and working towards something. A masters runner, let's face it, you're not going anywhere. If you weren't a "name" runner in your youth you're really not bringing anything to the table and some old guy wanting to save a few bucks on races really isn't trying to improve the sport, he's just trying to improve his bank account.