Depending on your climate, 8 years is a long time to go without maintenance.

There seems to be a general concern of global economy, etc.What are your thoughts on how this climate is going to affect Real Estate market in the near future ? 

Times change, market climates change.

there are no jobs here (besides retail sales jobs and government jobs)... taxes are ridiculously high... the climate is cold... houses are ridiculously cheap (I can buy a waterfront house with a boat dock for 170k; I can buy a single-unit fixer for 30k).

And I think you can buy the buildings cheaper too because they don't have to be built with the construction used in cold weather climates.

IIRC he had netted about 5%-6%/year.BTW, both of these guys did some of their own work, annual painting, some of the appliancce updates etc, during their "off-peak" stays.While we're actively looking for a "second" home in a more moderate climate, both of our places will be strictly for our personal use.all cash

Just look at what Dodd-Frank did to businesses engaged in seller financing, what laws in some states have done to those going after pre-foreclosures or just the basic change from buyer's market to seller's market over the past couple years -- if you aren't able to adjust your business to the changing climate, you're going to find that what was a stable income can quickly go away.

What weather/climate issues might be a major headache that I wouldn't know about?

In use in all sorts of climates.

We found with the change in market climate.