Some will end up making a killing.When it comes down to it, a tech bubble burst may only really affect the housing markets where there is little economic diversity (Silicon Valley).

Should I call out the damaged items during the walk through?

Junk yards typically have battery acid leaks, motor oil leaks, gasoline spills and other items relating to electronics.

This budget works depending on the area you are looking.If you don't like how your agent is performing, then get another one, but ask yourself are you being realistic in your search (An example would be looking for a duplex in Northern Liberties, or Point breeze with your budget and all your wish list items checked.

I called several lenders and one was 75% LTV, one was extremely slow so I pulled the application, and another was 80% (who I went with).The refinanced property had everything practically new (wiring, plumbing, kitchens, bathrooms, decks, etc.) with few items less than 5 years old (roof, siding, furnaces/AC), but the windows were 10 years old. 

This is one of those major items to double check for when calculating repairs and making an offer. 

I recommend having a diverse portfolio!

If your looking at a syndicated fund there are some definite items to keep in mind.

What items will they not cover?  

I'm not sure where you are and if Chicago is close for you to benefit from it's diversity and population growth.