Wild thread, OK on first topic the trees look bad but not the worst I have seen. On Bradford Pear I have done similiar, bit deeper in the middle to remove more included bark, they might look funny in the winter but they come back nicely in the spring and hold together in the wind. Would not recomend it as a standard practice for tree work. Just some folks like that type of tree and pay to get it pruned every few years.
As for Muni-tree vs private-tree company owner, I am both. Work for the city days and run my own show after work and weekends. Licensed, insured, all legal. City job pays health insurance and mortgage and private pays the schools, food, electric, ect.. Muni job is thank-less task, management has no idea about tree work and usually very little about management. As for killling yourself physically on a muni job, does the word semi-retired hold meaning? There are days when muni-workers earn their pay, storms, nightwork, etc, but it is not like production work. Muni-work is all about politics, take care of the complainers so the noise does not get upstairs. There lies a major difference between privates and muni. On a private job, citizen can be screened before doing the work and if necessary ignored. Pack up and drive away. Does not happen with muni-work. Does not matter how obnoxious the public gets, job still has to get done. Other difference with privates is the ability to walk away from hazard job and give it to some one else. Muni-job usually does not have the same option, there is no one else. Depends how you look at it but they both have ups & downs, no pun intended.
On to other sub topic about small business, this country was built on small business, the difference today is that many are not legal. Pricing work just to pay for gas, beer, smokes without overhead is what is killing this industry. As much as ISA and TCIA do to help educate the public about trees and safe work practices, they need to take some membership $$$$ and start focusing on the hack tree services that keep popping up killing the legit companies.
Rant over, nuff said