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Think outside the box. Weddings, portraits, and all the "Usual" stuff is going to be done by every momtographer and department store button clicker in the area, for much less than you could make a living with. You have to do things that no one else is doing to make some decent money.
Sell shots to local shirt printing companies. Write up a contract saying you get X% of the sales, and it's free, passive income.
Make prints and sell them at a local music and arts show. One of my buddies makes print transfers onto chainsawed tree trunk rounds for $200 a pop. I just print out some macro nonsense and hipsters eat that shit up. I sold a 8x10 picture of some cigarette ashes for $75 to a big, beardy fellow who was smoking.
Submit shots to cash/merch winning contests. Sell the merch if you don't want/need it.
Talk to some college bars to see if they will let you shoot pictures in their venue, then set up a print station outside the exit around 1am. Sell $5 4x6's. Drunk people (especially drunk college girls) buy stupid shit.
Get in with some people who still have siblings in high school. Offer to shoot pictures of their band/football/basketweaving events, and sell prints to the parents.
Shoot every single local event you can think of (parades, famous people appearances, house fires, opening of the 18th Starbucks in town, whatever), write a small article on the event, and sell the picture and article to a newspaper.
Take every single dime of profit that you make from photography, and invest smartly in stocks, or put it in a compounding interest bank account.
