If you look through the Disney lore you will find stories of cm's whose job was to paint the hitching posts every night before the next day crowd arrived. They would go as far as doing calculations to to determine how long it would take something to dry based on the temperature and relative humidity at the time. This way nothing would be wet when guest began arriving in the morning.
Unfortunately, these days are gone. It just became too unrealistic, as the parks grew, to paint every chipped surface every night. One reason is that as the parks became more popular, they stayed open later. This reduced the amount of time for overnight maintenance both for logistical and guest satisfaction issues. A guest might not think chipped paint is very attractive, but they would be even less happy if their new white outfit was suddenly covered in black paint.
Secondly, its a labor issue. Labor rates have gone up for painters and other employees alike. But I would be willing to guess that park prices did not increase simultaneously at the same rate. If they had, very few people would be able to afford a Disney vacation these days. This means Disney has to pay more employees less money and not be able to attract quality tradesmen or they have to reduce the number of maintenance people in order to meet market rates.
It is the latter situation that DIsney has been working with for quite a while. For example, about five years back bus drivers' starting pay was near 5.95 an hour. The market around the country was 8 to 12 dollars an hour (even 5 years ago). New Disney drivers currently get $7.85. THis situation applies for many positions in the parks.
The bottom line is we can either accept the fact that Disney has to design a maintenance schedule for non safety related items that involves things looking a little worn form time to time ro be willing to cough up a heck of a lot more money for our vacations.