It still burns me to think of $250, but such is life.
And broken arms and ribs usually cost more. :P
The OP's first post may be throwing a huge flag on this play. There is a strong chance that the "handyman" with the $250 estimate has about zero in the way of coverage including liability or workman's comp. when it comes to the specific act of him playing "tree surgeon". Now the guy may indeed have a general liability policy, and be covered for a million bucks or more. However, that does no mean that his insurer is aware that he performs high risk work, or is insuring him to do so. A legitimately insured roofer, or tree surgeon, spend a mind blowing portion of his gross business income on liability and workman's comp. which is why a lot of them do without, and have much lower rates. Given the situation, I wouldn't contract with anybody without proper certificates from his insurer, and a conversation with his insurer, confirming the fact that he is fully covered.
After thirty years as a professional tradesman (electrician, builder, etc..) I damn near killed myself on Oct 8th. I had a 24' extension ladder extended into the loft of my garage. My head was about 16'-17' off the concrete floor below when the ladder kicked out from under me. I woke up about 45minutes, to an hour and a half later. Having failed my first attempt at human powered flight, I was rewarded with a concusion, probable hairline fractures in a foot and a hand, and a bonus of six or seven horrifically bruised areas including a 3" x 24" black stripe across my back, just above my 'plumber's crack". This was followed by a really fast ambulance ride to the trama center, five hours of various pokes, prods and tests, a parting comment that pretty much went, "you are going to feel, and look, like a bag of hammered shit for a few weeks, but you are extremely lucky to be relatively injury free". The total tab was a touch under $7K. Fortunately, the wife has great family coverage and it wasn't to hard on my wallet.
So, as you might imagine, IMHO, when I have tree issues in the future, I have come to the conclusion that the professional services of a highly qualified, fully insured tree guy are pretty reasonable.