Do you mean 5 cases or five counts? The state and the defense attorney can work out a plea where some charges are reduced depending on the evidence, his background and mitigating circumstances. There are lists and clinics that you may wish to look into. Your son's father should be able to at least obtain a public defender by signing an affidavit as to his low income.
Most likely they will file for a default judgment. They will get everything they want that is conscionable. You should immediatly file your appearance. It is simple and does not need a lawyer. Its on the cook county website. It's called an appearance form. Then you should appear at the next court date. The judge will likely not find you in default if there is an appearance on file. Worst case scenario you can always vacate the default within a specified period of time (dont wait more...
Don't introduce the significant other (paramour) to your kids until the divorce is finished, if there are any, and you will be fine. What you do on your own free time during a divorce is your business. It is misdemeanor, but i have never seen a single person be prosecuted and such crimes are outdated and archaic.
Couple questions. 1.) What were felonies for? 2. How old are you? 3. Which County did this occur in? As long as you were not on probation/conditional discharge/ or supervision, I think with a decent attorney you should not face any jail time. But these factors you attorney must before proceeding ahead.
You should eradicate any contact with this person especially while on Parole. I would ask your attorney to contact your parole officer to illustrate that no foul play has been done on your part. With respect to the eaves dropping issue. It is unlikely, but I don't know what charges your faced.