Unfortunately it is a condo. I've been taking pictures of what it looks like now with the tarp and existing step flashing still present. If I find out they're planning on reusing the existing step-flashing, or if I see them do it then I will complain about it. If that actually were the plan, I would never have wanted them to work on my roof at all, since they may be making it worse than it already was, since it didn't leak when it rained, just when ice damming happened.

The person who works for the management company told me that this is a preferred contractor who would never put his name on anything unless it is done right. Should I really trust this?

My opinion is that if the job really does require removal of siding to be done properly that should be done regardless of the price. However, the roofer seems to be assuring them it will be "done right" without removal of siding. He supposedly tried to locate matching siding and now is claiming if siding is removed it all has to be removed and new siding put on for thousands more dollars. Not sure I'm convinced that all the siding really would need to be replaced if they could locate matching horizontal cedar siding. But, if that really were necessary to have it done right, and they don't do this, then it will still be more expensive for the association to have to do the work all over again a 2nd time when it leaks again.