I've done both W2 and contract work, most of the contract work was earlier in my career, now I need the benefits, married mortgage and kids.
Don't do 1099 you leave to much on the table, do Corp to Corp much better rates and better write offs. Also a lot more opportunities.
I pretty much work in the same stack as you .Net full life cycle with a web centric focus, I am always in the finance space. There is plenty of opportunity if you are willing to jump around and take lots of short term gigs and are ok with breaks in work while find new jobs. How that equals out in the end is the end game.
Good luck!
-Mister FancyPants