It is one of the main reasons why many do not do these events and some of those who do we pay for them out of pocket. I completely agree that it is a fun way to share and get to know the community, that is why many users look for a delegation or the support of a whale to be able to continue these events.

What I recommend to do three options:

1.- Your voting plan for the winners seems good to me but you have to think that the publications that are being added will run out of time and at the end of the contest and get the publication out with the winners maybe the winner will be late to have If you voted, I think that all participants or at least some of the entries should reach you in a smaller portion than voted by @steemcurator01.

2.- And at this point, if you want to help with the collection of the money to be delivered, you can do so without taking it directly out of your pockets simply by voting for the publication of the contest, which usually from there the creator of the event can get the award to deliver to the winners.

3.- It is clear that the user who comes to steemit likes to write or has an area in which he stands out and wants to share his work with the community and added to that leaves him some money is better. One of the ways it can be handled is with a delegation to the accounts that are in charge of carrying out these events so that they can assess the work of the participants or simply following a voting trail.

This is just a recommendation and analysis to your proposal, maybe some improvements that could be made to the original idea, which is very good, but it will give you a lot of sure work and you may have to think about delegating these activities to other people or communities and you supervise their work, saving you time to administer and manage other tasks.

Regards...

Electrodo