Rogue condo presidents

We have three condo sub-associations. The board has a good relationship with two of the three. The president of condo 3 (he's a good one) has long been upset because the master association owns the roads and the gutters (there are no sidewalks or curbs, just a v-shaped gutter at the sides of the roads). On a corner in his area water from their sprinklers collects in the gutter and sits there. Gutters are designed to clear after 24 hours. This one doesn't, partly because they water very heavily despite our request for them to reduce the water. Our resident civil engineer, who spent most of his life building roads, says it's a matter of overwatering and we don't need to fix the gutter. The condo president insists we do. Last week, he and the other good condo president (condo 1) went to the area with a drill and drilled 1 inch holes all over the gutter so the water could drain through the holes into the ground. They got caught by the PM, who reported it to the board and made the two condo presidents send an email admitting they had done it. We don't know what harm this may do - the big concern in Florida is we do get very heavy rains and if the water drains behind the curb it could wash out the soil and cause a collapse. However, we think maybe the holes will just fill up with sand and debris pretty quickly.

Then today I found out that the condo 1 president took it upon himself to do some landscaping at an island on a side road leading to the commercial area. We do not own this side road. There was a defunct commercial owners association that has recently been reinstated. We have been working with our attorney and the commercial owners because this road is attached to our privately owned road. Granted, the island has not been maintained, but he didn't check with us or anything - just went and cut down weeds and plants and then asked his condo landscaper to pick up the trimmings.

Clearly the hole drilling was vandalism of master property. And the landscaping was trespassing on the commerical property. Any suggestions for getting these guys under control? We have been very good to them compared to the last president. Maybe that's the problem. Any suggestions on how to get them under control?

If these two are normally good at their jobs, I suggest sitting them down and spelling out the possible consequences of their actions, including to them personally if - for instance - the drilled out area does become unstable. I harp on this a lot, but folks tend to come up with solutions to their immediate problems without thinking beyond that and can end up with even bigger problems than the original one. With luck you'll end up with more knowledgeable folks in charge who will make better decisions in the future. And if Mr. Drill Bit worries every time you get a downpour? Good, that's his punishment - no need for the association to get heavy handed when natural consequences will do the job.

(This is another example of why I'm so against volunteers doing physical work. The risks to the association outweigh any benefit from their "free" labor.)

Take a look at it from their point of view as well as yours.

Regarding the drainage, The water sitting is an issue. If water sits with supposed over watering, water will sit with heavy rains as well.
Therefore, I don't think your engineer is telling the whole story.
My suggestion - come up with a plan to have it drain properly (groves in the gutter to help slope and channel the water is one possible option that would be less expensive then redoing the whole curbing in that area).
Tell that sub-association to repair the damage and, ideally at the same time, provide a plan to try and address the issue.

Regarding the landscaping -
Forget about it.
If anything, it's an issue between the sub association and the commercial association, not the master association.
I expect that master association funds were not spent.
I expect that the master association doesn't have standing to complain about trespassing (as it's not their property).
I expect that the sub-association was tired of looking at common area not being kept up and, per your posting, no one to address the issue until recently.