If your roof is in good repair and not at end-of-life, it should be able to handle the average, think up to golf ball sized hail for a few minutes - Texas hail storm. 

If the owner says he's interested in selling, I personally would not muddy the waters up trying to talk about a low ball price.  

Just curious: In cold-weather parts of the country where winters go below freezing temperature, is it typically easier to negotiate lower purchase prices during the winter months?

The thermostat is located in one unit, who is instructed to leave the heat set at one temperature.  

ITs a small community if you get black balled for writing offers and tying up properties then never closing it makes it harder down the road.. and makes it harder for others as well.

Present a low ball cash offer, knowing they are probably going to try to haggle a better price?

Anyway, I'm happy to meet you at the property if you'd like to do a quick walk through and give you some ball park numbers. 

While I can be rather bold (LOL) I was a ball of nerves knocking on the first few doors.

I won't pretend to have a crystal ball, but since you're asking for gut...I think the market is turning from fiery to just hot, but directionally cooling, and (un)affordability on the Peninsula is creeping into 2004-2006 levels, so I don't predict a long, hot run ahead of us for the next 9-18 months.

Some counties are so far behind, you can go a couple years without them doing anything, and others are on the ball and will sell it right away.