Wearing too many hats can hurt your head

Well, I really feel that this is my kind of group, I have been operating a gaming business site for a few years now, originally it was set up as a profit-share for local players who paid a membership, any revenues that were created were paid out in the form of entrance fees to live tournaments, not just locally but as far as Vegas and part of the deal was that any winnings, a percentage was to be contributed back into the pot. This worked well for the first 18 months and we had approximately 14 members, but unfortunately it was 3 or 4 people were doing all the work whilst the rest reaped the rewards, so I made the decision to "pay off everyone" and go it alone. This was fine initially but as the site grew I had to take on a couple of people for various aspects, Ie web designers, site moderators for the forum etc etc. but as I was only paying on a sporadic basis based on the percentage we were bringing in, and believe me some months it was zero, people lost interest. I am now in the situation where I have to bring in a total of five people to handle various jobs and I am reverting back to a profitshare system, however after a consultation with someone I can only say is a "Gaming Site Guru" I have to lose my nice side and really make sure things happen and if it doesnt then I have to put on the "sacking hat" Sometimes its hard to let go of what you can only call your "own baby" but at the moment I am just trying to do too much and all that is happening is I am diluting each process.
Without going into the actual mechanics, I had a carefully mapped out joblist, and of course, several unplanned factors jumped into the equation, so I am now sat with one third of the list done and two days behind.
I know that planning is important and a little tool I usually use is the urgent vs Important matrix system (If you haven't seen it before it may help) 4 little boxes but it sure helps you to prioritise.

Time Management Box

I think for one man businesses, the most important factor is to recognise when you DO need help and to get that skillbase in, obviously this can be something that occurs over a short period of time or on the other end of the scale maybe it is something that can be ongoing, either way I certainly think that a lot of people put off expansion on staffing too often and in some cases this can be detrimental to your business.
I hope this makes some sense and I look forward to hearing everyones thoughts