If I were a gambling man Mike, and I were looking at CT, not just Hartford, from 3,000 miles away (with limited direct knowledge and experience), I would bet that when CT finally turns over to a more business friendly climate (ie, oust the liberal - long held democratic views), we could be just like you in CA :-) In fact, if I recall CA was in some major trouble 10-15 years ago too, and now look: 2016 San Fran became the very first area to have average home prices over $1 mil. 

You all touched on numerous points :) My investing strategy is as follows: 1.

This site is an incredible platform that has numerous resources so definitely take advantage of it all.

If you're ONLY searching for duplex properties you're competing against numerous investors.

I wouldn't recommend going into someplace that has no policy concerning STR, as it's a huge gamble.

I've seen it firsthand on numerous occasions in numerous basements with uncovered cleanouts, etc. 

I am involved in numerous syndications so am very familiar with the structure.  

The cash you can "Throw at this" will probably figure into it, unless it's some type of high risk strategy where you have to do X a lot times in hopes of getting result Y (in which case it's more of a gamble than an investment).And as Kenny Rogers said in "The Gambler", "You never count your money when your sitting at the table".Kenny Rogers "The Gambler"But if you are gambling, then realize that sometimes gambles pay off and sometimes they "Crap Out".Good Luck!

While the potential increase is a gamble from zero to infinite, the security of not creating a lease no longer appealing to the company is guaranteed.

I've read numerous posts on Biggerpockets with estimates and lessons learned in other cities, but nothing current in DC.I'd love to hear any recent experiences digging out and underpinning in DC, including costs, contractors (referrals very welcome!)