My issue comes down to just loathing the process of applying for work . . .
So I don't know that anyone can really help me, but any advice, etc would be welcome. I just need a bit of a kick in the ass or something. Something to recharge me after work seems to suck my soul away.
Your post resonated with me. I have been an IT Contractor for 20 years. You are reading a post from a guy who regards the job search as akin to having a root canal - only most people would rather have the root canal. That said, I am happy to share what I have learned over 20 years.
The number one thing that has allowed me to hop from one contract to another is having a perfectly tailored resume for every job that I have applied to. Hit them right between the eyes with what they are looking for. It may seem childishly simple, but it has worked for me beautifully. Remember, the job requisition was written so long before they received your resume, they have no idea what it even says.
The second thing is keeping track of all of those resumes. A spreadsheet used to be enough, but it is no longer. There are a lot of excellent software packages that will organize them for you. Go to the Resumes section of download.com and find one that fits. JobTabs works for me, but you need to get one that works for you. Tracking all the resumes means knowing what is inside them because you want to keep all of the "Word Smithing" down to a minimum. All of the editing is one of the biggest drags on the job search and you absolutely, positively have to keep this to a minimum. When applying to a job you have to tailor the resume that best matches the job requirements. After about twenty resumes, you will pretty much have engineered all of the tailoring out of your job search.
The third most important point about landing a job is to apply to lots of them. Once you have enough resumes and have enough cover letter templates, applying to jobs is a cinch. When you get shut down or never hear back, you will not be demoralized because you have so many irons in the fire. This is also the best way to get a raise. When you have competing offers, this is the best time to find out what the high end of your skill set is worth. Once you know you can get it, then it will be that much easier to ask for it again and again.
Rugorak, get out of that hokey pokey little town. It sounds like your life is passing you by and I'll venture that it is! :-) Consider moving to North Carolina. Great mountains, beaches and everything is dirt cheap! : -) Everyone here is Mr. Money Mustache already because there is nothing to buy!
Good luck,
MountMitchell : -)