This place needs some beautification. The question is, will association members want to pay for it. A major, major item you left unsaid but expensive to maintain are miles and miles of where blacktop meets grass.  

About ten or more years ago a GM asked for the budget to include eight employees to do no more than maintain roadside ditches. The board gave him four.

I suggest that to keep the roadside grass looking good and cleaning up the matted pine needles along many miles of road edges would probably take a crew of 20 or more. People do not want to pay for beautification, real beautification, beyond planting a few flowers and trees.

some solar lighting at mailboxes

Not sure how those with mailboxes next to their homes would see that as an improvement.