I check both spots for a sign of moister or a leak.

South Side has a reputation as being a pub crawl for college kids, but also has a high density of boutique entertainment/retail and is very walkable, yet still a few miles from Downtown.

Maybe I could help, maybe trade services, I.e. website/data to market for a camp ground spot :-).   

If youre not married to the wood and you want to start over, AND you have "soft spots"...I would rip it out.That way you can put in what you want and it will go in right without affecting door gaps, cove base, and the like.

Everything @Nathan G.said is spot on.

The property I am looking at has 4 spots that will need to be addressed, two are on an outside wall, one potentially in the kitchen ceiling and then in the unfinished basement.

Make sure with their company they do not push you off onto a newly hired inspector and demand you want the experienced person to conduct and look at the property.Sometimes the company has great experience but the worker is inept so you have to watch for that.Inspectors usually charge based on the sq ft of the house and if they have to crawl under a foundation or it has a basement etc.

If a seller has a three foot hole in the roof that a five year old can spot this is not required to be disclosed.

Granted they are a bit closer for the actual claim of wind damage in order to do some of the repairs is more than refastening siding and patching a few spots on the roof and walls and painting"What should we do now?

@Steve Vaughan is spot on.