I've been in IT for 17 years, and it's done nothing but become harder and harder. I've been with the same government agency since 2000, being the Network Admin (as in, the only one) most of that time. Until 3 years ago, I was the only full time Windows guy. Until 5 years ago, I was the only Windows guy. We now have a manager, a programmer, net admin and a net tech.
Everything is continuously growing, and more and more systems get added or expanded. When I started, we had a small token ring network, 2 Windows servers and 1 AS400. It was like most other systems out there; Microsoft Office, a few network printers, and not a whole lot else. We now have 6 VMWare virtual hosts (with two enterprise grade iSCSI SAN units) running 36 virtual servers, with around 12 physical servers remaining, and the network has been overhauled twice. We now span 6 facilities, with fiber running everywhere, with 3 layer 3 chassis core switches, and over a dozen light layer 3 switches throughout the company, with a WiFi radio network running across 28 Access Points and growing. We incorporated a complex Computer Aided Dispatch system (public transit) 9 years ago that started with 3 servers; it now has 8. That's just the tip of the ice berg.
Honestly, I frequently think about getting out. It really can be brutal, and while you know you're a miracle worker (and some people recognize that), people always expect more AND your work is mostly not visible and virtually non-quantifiable. Even the things that can be seen, such as the glorious servers and switches, are hidden behind doors. I have a relatively young family though, with a stable job, good benefits, and reasonable pay; tough to walk away from.
So, with the griping out of the way... There are steady jobs out there. Many of my friends are in IT. The bigger the city, the easier it is to get in. I don't know about getting in without going through bottom rung support work though. I had hands on server experience when I started here, and worked on the servers right from the start, but it was a few years before they officially made me the administrator. Even then, with as thin as we are, I still have to do helpdesk work (I'm not much of a people person myself, but I somehow excel at customer service.) At the very least, I'd think you'd be looking at starting with bench work, fixing desktops and laptops; possibly at a depot where systems are shipped in and out at a fairly quick pace. Education is probably the only way around that, and even with that, I would think the best entry point is still through either a massive corporation or through a contractor.
FWIW, Knowing Windows Server 2008R2, Server 2012, Active Directory, Hyper-V and/or VMWare seems to be of utmost importance these days if you want to touch servers. Network engineering and security are big as well. I still run an Exchange server here, but that's getting outsourced more and more to the cloud; I wish we would, as email is a nightmare.