The kitchen with the black-painted cabinets look great, but is that because it says trendy, or are they inherently better looking than natural wood?  

Bullet Points for St Petersburg:Short term rentals (anything less than a month) are technically illegal, but...Code enforcement only enforces this on a "by complaint" basis.The City can't change this law in any way (in either direction) without risking losing the ability to regulate short term rentals altogether, so...We have a thriving Air BNB "black market", but it's inherently risky and you should not base your long term cash flow numbers on this model...the smart strategy seems to be get it while you can, but be prepared to quickly shift to a long term rental strategy if you get busted. 

Then repair roof outside, black tar if you have too.

@Wendy Black The crime factor is not necessarily a deal breaker.... that being said it can be scary. 

Some initial thoughts would be to cut back the trees/brush to the right side (near front door) to give that area some more space and a welcoming feel, rather than walking into a black hole. 

Are you implying that we should try to be on black for line 26 to look good for financing.

Either way, having your name appear on the state database for unlicensed activity is a black eye.

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.