Exactly, that is my concern, but struggling to find a company online in the Boston suburbs that seem to remove large antennas. If anyone knows the name of someone qualified to remove these please let me know
Don't screw around with amateurs if you are concerned about liability, something getting damaged, someone getting hurt, etc.
The correct way to do this would be to talk to one of the companies listed on this page:
https://natehome.com/locate_members/results.php?ID=21
The National Association of Tower Erectors is an industry group for tower companies. The companies on that list (all in Massachusetts) will have the proper certifications and insurance to do this type or work.
It'll cost more, but you'll get professionals that know what they are doing.
Amateur radio operators might be able to do it for free, but it's rare that any of them have any formal training, and more unlikely that they are certified climbers. I won't even touch on the insurance side of things. Getting a hobbyist to do it for free might get you some guy that's just eager to get some free stuff and might cut corners or put others at risk.