You'll have to recapture it if and when you sell, but it's merely a loss on paper and can bring you back in the black in a case like this, so you likely wont lose money.  

The strategy is best described in Joel Greenblatt's fantastic book, and an outstanding practical guide and tool for executing it can be found over at the Magic Diligence website.You can do either (or both) of those using the "leverage" of Options, allowing for substantial upside potential compared to standard stock purchases, with dramatically reduced downside (if you want a no-hype education on Options, Erik Kobayashi-Solomon's book is great).Those with the patience and inclination can indeed use Option trading to make money in any market condition (Wikipedia founder Jimbo Wales, Amazon's Jeff Bezos, and "Black Swan" author Nassim Taleb all spent time -- and made lots and lots of money -- as options traders in their careers).For even more leverage, you could of course do any of the above (and much more) on margin (meaning your brokerage lends you money to do the investment), though that's not something I would ever do personally.Also, if you focus on holding stocks (or options) for at least a year, you benefit from favorable tax treatment of the profits.

Danny, sounds like you've got some great goals and even experience so far.Since you mentioned meeting others with similar or more experience I'd recommend a local investor group like RIREIG in RI or Black Diamond REI in southern Mass.Both are good groups that are education oriented (don't try to sell you stuff) and have members with a wide range of experience who may be able to help you reach your next goals.

BTW I spent about 7 years working in Black Hawk and never lost at gambling.

This may or may not apply to your situation, but for me, I think those decisions are more personal and not a general right or wrong, black and white situation.

It's no different then rehabbing that first house and finding the black mold mess once you pull that first strip of paneling off the wall.

Inside is a simple black-and-white letter with my signature at the bottom.1.

Yesterday tenant called me to say there are mushrooms growing out of the ceiling where the mildew is (I'm calling it mildew, he's calling it black mold).

Most tenants are good people, it's the "hope for the best, plan for the worst" that is worth pondering.I'll try and put it in the most black and white terms possible. 

I'm not in Massachusetts so hopefully some locals can chime in here, but it sounds pretty black and white to me.