We've had a few roofers out and all have said that if we choose to repair, we will likely have to repair again in a year

Had we missed our window, it would have been a couple more weeks.Good roofers will work in any temperatures, as long as there isn't snow on the roof.

@Fil Mendes , I'm very sorry to hear about this.

To be honest, I have had inspections that were missing key things (like the inspector who was too robust/heavyset to go into the crawl space to discover that all the copper plumbing had been ripped out), others who found the obvious (the plumbing should be replaced...no duh) and others who were pretty useful (the chimney is falling over so it would be better to get the roofers to tear it out and cover which saved me a ton of money).

My roofer tells me he can be out there in a month to look at it.

I am just starting out, and wanted to know if it would be reasonable to negotiate a decrease in sales price given the inspection findings, without having a specific roofer, electrician and plumber come out and give actual quotes for the work that needs to be done. 

We lost $1500 straightaway on a rogue roofer.  

I sent back my roofer and he applied more sealant.  

It can be tough juggling contractors, electricians, roofers, etc. without have a VERY clear idea what something may ot may not cost.

Not to mention, of the more dangerous jobs, many have lower average salary, including coal miners, loggers, roofers, and electrical pole workers -- all honorable and tremendously important jobs in our society.