Lance, I don't know what size outfit you've got there. Here I've got 4 trucks, a skid loader and 14 or so pieces of eqpt with small engines of one sort or another.
I have no formal system like Paul's (and we're not as big as Paul's outfit), but at the beginning of each season I set aside one day per month for maintenance. I have no set formula, but everything gets cleaned, and those toys that have had the most use over that month get oil changes, maybe the air filters replaced.
I'm jealous just seeing that you're in Hawaii - I've been to Maui 2x and look forward to a return, maybe to Lanai. Any recommendations for a place that is remote (non-touristy)?