How difficult is "reentry" for someone that's been "out"
I'm a middle-aged tech-geek female that took time out to get the kids through school, and get my college diploma completed to go with my previous experience (20+ years,I've done database management and administration, information security and contingency/disaster recovery planning and some data analysis).
How hard is it to get back into the IT world again?
By all means, try, but . . .
. . . don't blame yourself if you don't succeed. Getting back into IT after more than 6 months is next to impossible even for younger folks, even in the best of times.
...doing short term contract work (through a large firm like Robert Half or Ciber). They'll take care of the hard part (getting your foot in the door), assuming you can prove to them 'you still got it'.
After a few 'wins' or a year or so, it should be much easier to sell yourself for a full-time gig, assuming that is the route you want to go.
Volunteer work (churches, nursing homes, etc) is also an easy way to get the resume 'modernized'.
If you can land a job and were good at your job previously, then you shouldn't have too hard a time of learning and updating your skills. Maybe take a workshop to update your skills and pop a certification on your resume.
You could also accept an entry level position to get your foot in the door if you can find one. That way you have a good chance of getting a job, and can update your skills without the company taking too big a risk on you, then, once you are comfortable with your new skills you can look for a new job or demand more money and more responsibility.