Well I just had a 3rd company show up to look at the job and give me a quote. Looks to be in his 50's and a seasoned builder. He didn't seem to thinking raising the roof was a big deal, and even said they can save and reuse some of the materials. What?!
I told him about all the options I was considering. He seemed to think they could raise the roof cheaper than building a new metal building.
He didn't give me a quote though. He wrote down measurements and said he wanted to work on the numbers and try to have a quote for me by next Friday.
I hate waiting, but I'm really interested to see what he says.