I'll tell you what I know...or think about session players. For one..nashville is a different market for session players and not what I would consider the norm.. But I mention nashville because the session players there (the A team) are top notch and basically are on ALL the records that require session players. Outsiders..take note... (in other words...find another city)
But...being a session player (especially on guitar) is probably going to be rough, unless you are very experienced in a wide variety of music...and I think being able to read GOOD is VERY important. Unless your ear is beyond great to not require reading. But, when a client comes in with a chart with a tune you've never heard, unless you can "wing it" without reading the chart somehow, expect to be up shit creek. If you are just looking to be the man with the "hot licks" for some group, expect that you'll be competing with the groups guitar player anyway, and in about 100% of the situations, they won't be looking for a session player anyway.
Myself, being from another decade, the session players I've been aquainted with and dealt with, did jingle work and stuff of that nature. Vocalist are MUCH more in demand. Someone that can sound PERFECT and sing: "oh..those burgers are better at Charlies cafe...."
Take a look at the talent in Boston. A zillion hot reading guitar players. However, most of them don't consider session work as viable music and pass it up. GREAT session players make GREAT money. So so session players never get hired.
That's been my experience.
Yeah...your CD is killer, your music is good...but can you play like Joe Pass, Chet Atkins, Van Halen, and a little of Metallica for those ESPN backdrops and maybe even a little bit of Muddy Waters with a sprinkle of Segovia on top?
Not to discourage...and certainly do the above suggestions, because without doing them, you'll never know. Plus...I've been wrong twice this year so far!!
I think "sticking" your foot in the door...rather than "getting" a foot in the door is going to have to be your route. Make things happen, not because you are good, but because you are saavy.