IMO you're right about digital but you should prioritize thinking and portfolio over acquisition.
I've twice started successful free-lance business, two different cities (Santa Rosa CA and San Francisco CA), two different kinds of work (architectural and commercial/product/food).
You need to prospect for business by the numbers, not by referral and rumor. Make a long list and see everyone on it, checking off the list. No shortcuts. Most photogs are reluctant to get out and seriously sell themselves, so if you step up to the plate you'll beat them. QED.
A fine (then) young architectural photographer told me he'd immediately become successful by showing his work to forty architects a month, doing little else (it was hard work to get in front of every one of them) for TWO MONTHS. He was the finest of B&W large format photographers, Imogene Cunningham's printer, which helped socially/artistically in San Francisco. And he started out with good 4X5 equipment, having made a point of studying and copying the work of other architectural photographers...which justified his claim of competence.
I tried to follow his advice in Santa Rosa, a much smaller town (maybe a total of six real architects and another six "building designers"). My work was nowhere near my friend's in quality, but it was marginally pro quality, adequate. I learned. I abandoned that business after two years because I wanted to get out of the small city and move back to San Francisco.
A dozen years later I did it again in San Francisco by developing a strong, graphic, unique portfolio and showing the bits and pieces I'd done on the side for years as crappy portfolio. My work was fairly good, middle priced in that market (ie $450-650/day in 1978-82). Every time I did a job I tried to do something with it that would produce a portfolio piece, no matter the intentions behind the shoot.
Importantly, as I went along I made a point of getting close to local "foodies," chefs and cooking-school teachers and ad agency art directors, as well as people who were pure graphic designers, not jacks-of-all-trades, so needed to work with photographers (and I understood the details of their work, which was key). I quit because I got fed up with client relationships. A better person would have done better with my opportunity.
I've recently shot a wedding and some babies, as well as a couple of portraits. I have a somewhat formal family shoot coming up. Just folks. I'll do it my own very narrow way, 35mm B&W and inkjet on watercolor paper. When I was a kid this stuff was beneath me, but what I most want to do these days is photograph plain people with some kind of honesty. This isn't biz, though it may become that slowly, if I live long enough.
