Stop whatever you're doing now and read this book: "The Practicing Mind: Developing Focus and Discipline in Your Life - Master Any Skill or Challenge by Learning to Love the Process" by Thomas M. Sterner.
"What's left is real estate, but I'm regularly told I shouldn't even bother if I'm not a fix-it handyman sort, which I'm not."
You don't need to do the fixing yourself... My advice would be to read 3+1 Plan book (http://en.wikipedia.org/wiki/The_3%2B1_Plan). You can get it for free in PDF from the author if you sing up for one of his websites.
Looks like the 3+1 Plan is basically to buy a property, pay interest only, wait for it to appreciate, remortgage, use proceeds to buy another property.
I think I'm looking for more detail from a hacker perspective - how to get access to RMLS systems, mine the data, what kind of criteria to look for for best arbitrage, what kind of moves you can make if you have $x in capital, etc.
Here's my experience. If you don't have a lot time and not into construction and not a lot of money, don't bother going into foreclosure, flipping, or short term project. People going to court house auction bring in a million dollar cash to bid on foreclosures. They can keep bidding a house up until you run out of your reserve. It's very difficult to outbid them and still make a profitable flip.
For casual investor, the best approach is just buy and hold from the regular market, utilizing long term leverage to gain the profit. You want to buy into a trend and RE has very long trend. A rising tide lifts all boats. Doesn't matter which house you buy. It will go up in price in a uptrend. Also established neighborhood is easier to predict up and down. The whole neighborhood will go up in union. New development might turn out good or might turn out bad, depending on the people moving in.
For RMLS, the regular listings have a lot of information. The regular websites like Trulia or Ziprealty are good. Insider knowledge will not give much advantage because RE is a heavily regulated industry and once a house is listed, the agent has a duty to get the best price.
You're thinking about a scenario where you are carrying a hammer, and your looking for nails.
Real Estate is all about information. That information isn't in the MLS system.
Examples: How long is the old farmer by the interstate going to be around? What neighborhoods have weak neighborhood associations who won't protest my hacking a 2 family into a 4 family to maximize section-8 revenue?
my friend has been doing this for a few years but he's saying that opportunities are drying up with the housing recovery. Also he is a handiman so his margins are higher than the average person yet he's still seeing fewer opportunities.
Also keep in mind that brokers take ~6% on both the purchase and the sale of a property, which means that the property has to increases in value substantially for you to be able to effectively "flip" it. (rates are negotiable obviously, and I think you can get a certification to be able to handle some things yourself instead of getting outside service)
The investment works because in 10 years time you own bigger chunk of the asset (Mostly due to inflation but also debt repayment from rent).