Automating Process Improvements - Need Computer Expert Help

[Texsox]

When I'm not a suffering Sox fan I'm a high school golf coach. For us to play in tournaments there are 10 steps that need to be completed.  Tracking them all is getting more stressful each year as more requirements are placed on me. So I'm trying to figure out how to automate the process a bit more. 

Once I decide on a tournament I need to

1. Email Tournament Director

2. Download entry form

3. Fill out Purchase Requisition (Adobe Acrobat)

4. Verify PO entered by bookkeeper (received email?)

5. Arrange Transportation (on line form)

6. Notify Players (SportsYou chat for just those players)

7. Notify Attendance (email with names and student ID)

8. Enter Substitute Request (online system)

9. Create sub plans

10. Enter expense in ledger. Two possible accounts kept currently on a Google Sheet. 

Rinse/lather/repeat 70 times per year. 

I'm willing to invest in software, hardware, whatever to make this easier. I tried to have the school lower my coaching stipend so I could officially add a second assistant but was turned down. I may just pay someone on campus to handle it. 

I tell myself I coach kids for free, the pay goes for this.