Citygirl,
Real life is not like movies where somebody breaks the law and then police cars show up immediately. Illegality is more like playing Russian roulette, it is a matter of risking yourself unnecessary. Sooner or later you will have a problem because immigration inspectors do what they want. You cannot predict their behaviorist as you think you can.
I work about criminal law too and criminals commit many crimes until they are caught. Of course, at the begging they are stressed, later they see that nothing happens and they relax and start to believe that nothing will ever happens. One of my clients was a mule, DGM reports showed that he crossed the border over 50 times. He was carrying Cocaine, but he is in a Federal Prison nowadays and we are waiting for the trial. This is only an example about how illegality works. On the other hand,
a legal (or somebody who works about something legal instead of narco-traffic) can cross the border 1.000.000 times and nothing will ever happens to him.
There used to be a loophole,
now it is illegal to use improperly the 90 days staying. This is not a visa, it is an I-94.
The perma-tourist euphemism is something you invented to feel better about being illegal.
This is what a prosecutor said about a perma-tourist:
"regarding his illegal immigration situation"
There is no difference and no advantage about to "renewal" your I-94 going abroad.
So, my legal advice is: crossing the border is risky, do it if you want, you are an adult, but don´t be fake with yourself.
If your don´t abandon the country you become an inhabitant and then you are protected by law. And you can apply for residence any time you want or for citizenship after 2 years.
So, wasting time, money and risking your self pretending to be legal isn´t as smart as you propose.
On the other hand, it is possible to became legal in this country without marriage or children.
Regards