"Now I have another Rails project lined up for a NYC fashion site that pays about 15% more per hour than my day job"
Contracting is vastly different than being an employee. Your employer pays considerably more than 15% more per hour for you (employer portion of taxes, portion of health insurance , etc.) As a contractor you'll be responsible for those expenses.
Health insurance can be had for barely more than the cost of fuel I was using in my daily commute, which is $200/mo. Yes, I have to do my own taxes, and yes they'll be a bit more, but as a sole proprietor I can also deduct many expenses. It's pretty much a wash. I firmly believe people make a bigger deal out of this than it is, it's a fear thing.
But this is beside my point, I'm transitioning out from Windows dev, and it doesn't have to be some huge sacrifice like many make it out to be. I have a plethora of full-time work I can take in front of me if I wish, I decided the 1099 route makes more sense for me at this moment in time.
Is it weird that I love doing this stuff so much, that the simple idea that I can go work anywhere means I can go on a 2 week road trip and work while doing that is vacation enough? Granted, me from 2 years from now might have a different take. But the fact that 'work' means going into a coffee shop, staying at home with my dogs on the couch, or going into a cool co-working space and collaborate with like-minded people... it's like my whole life will become this big vacation. Because I really love writing software, it's just exhilarating. 'Work' to me is having to slave through rush-hour, deal with water cooler talk, walk into a sea of cubes in a faceless corporation, spend hours upon hours in meetings that accomplish little, then put on my headphones and pretend I'm somewhere else. The work itself is what actually takes me away from that reality.
i.e., if you make $50k a year, charge $75/hr. If you make $100k/year, charge $150. How much do you think an associate attorney at a law firm that makes $150k per year is billed out at? CPA? Management consultant? All of these professionals are generally billed out at a median rate of nearly $200/hr. And the top end is astronomical, like $800/hr or more.
The hardest part about software consulting/contracting is learning to say a polite "fuck off" to the people not willing to pay your price. Everything else is easy. Making some money is the easy part. Earning respect is the difficult part.
"No less than 5 offers" - CHARGE MORE MONEY. As an engineer it is your responsibility to the craft to increase the prestige and respect of the job.
I also have another client who wants me to bid shorter term work (they did offer at a rate that's 40% higher) but I told them to hold off for now because I want to get used to the new contract first and make sure I'm comfortable with the cadence.
Key point - I will consistently be raising my rate, but for now I'm making almost as much as my day job and working much less hours, and I need to get out there network, get good, etc... and the rest will come. I'm approaching this in a way that aligns with my own principles. I'm not trying to be a bottom feeder in this market. I just am getting my feet wet with a minimal portfolio and simply happy to be in a position that I can make the transition into something I'd much rather be doing.
This is in Canada though, so I'm not taking the requirement to pay for your own medical insurance into consideration.
I turned down that management offer, kicked butt where I could and got promoted to a principal engineer. It was at that point I realized I was in a dead end job, went nuts in my free time reading book after book, tutorial after tutorial... and two years later finally summoned the courage to do a Rails project pro-bono on the side for a small local marketing firm; for about 4 mos I was putting in 60-70 hour weeks between my day job and side gig.
Now I have another Rails project lined up for a NYC fashion site that pays about 15% more per hour than my day job and I've been contacted for no less than 5 full time Rails positions, one of which I interviewed for and turned down. The demand for this stack is fierce. And you know what? I'm madly head-over-heels in love with the latest and greatest the web has to offer (ie. meteor.js gives me goosebumps, and at the very least in the near term I want to do a front-end mvc project ala backbone). I'm not great - yet - but I feel like for once I'm really in the game. It's exhilarating. I feel more alive than I have since my early 20s. This NYC contract is about to be signed, and once that happens I'll be saying goodbye to the windows world altogether, join a co-working space, build a network, go to local tech meetups, etc, to ensure I have a steady stream of work. It also helps to have at least 6 mos of savings in the bank to mitigate risk.
Seriously, go thru easy/free books like Learn Python the Hard Way, Eloquent Javascript, Michael Hart's Ruby on Rails Tutorial, the tutorials on the W3C site. You should be able to do all that in a couple months, and that's probably 50% of the battle (okay - there's alot more, but once you have some foundation the rest will be much easier).
EDIT: Wanted to mention about the full time Rails positions, 3 were for small startups, 2 for larger companies. Naturally the small startups you can expect to take a pay cut if you're mostly maxxed out in your compensation in your respective area. But the 2 corporate Rails gigs the recruiters wanted to put me in at or slightly above my total compensation package at my current job (partly due to those being a mixed environment and needing someone with both C#/C++ and Rails skills).