Go with GC #2 but ask for references and maybe photos or a tour... 

These are sometimes good deals, more often they're just average because every broker that the seller called has called all of their clients and by the time it's all said and done everybody knows about it.The second is where a seller wants to sell, but doesn't want anybody at the property to know it's for sale, or doesn't want a bunch of tours, or doesn't want to wait for the broker to make up a full package, market the listing, take offers, etc.

I am a startup business for real estate virtual tours. 

Touring a place that doesn't present well makes it hard for the future buyers to see the potential of the property.

I've had other units with single panes in the past and I think that is probably the last thing on a tenants mind when touring.

Go on some property tours and see the kinds of assets that are available, at what price, where.

In my case the guy kept hounding me via email after a tour, and I told him one million bucks was my price.

Now, these are on the MLS, so competing against retail buyers.At the end of the day, say there are 20 properties that look good to me at the right price, I'm leaning towards doing the tour, estimating the cost to rehab, and then making quite low offers, in the hopes that at least one or two would get accepted at a price point that makes the deal work for me.So my question is, does this strategy (in bold above) make sense?

In your case if deciding to go remote to one of those cities it would be wise to tour the buildings you want to consider for purchase yourself and to interview property managers in person to get a feel for how they do business.  

In terms of what to do, I'm planning to spend the $50 for a title search and I have a local agent touring the house (I'll drive up if I can or as a follow up) and would plan to buy title insurance.