When maintenance is done haphazardly, incompletely or only when convenient for the person doing the work, what does this say to the tenants? How about, "we really don't care how he place looks, it's not that important to us to do it right and on a regular basis and we don't think anyone really cares!"
Success means having a regular monthly maintenance schedule and getting the grass cut, trimming done and things blown off each week or every 10 days or whatever is needed. It means the club house is vacuumed, the picnic tables are stained, the drainage ditch is cleaned out, etc., on a regularly scheduled basis. In addition, there items on the schedule that might happen once a year, quarterly, etc...
Contract with someone to do the maintenance
Develop a maintenance schedule that includes what needs to be done, frequency and approximate hours
Add a spring "clean up" and a fall "prep" schedule as well
Get approval from the offsite manager prior to exceeding the budget for monthly maintenance hours