I've liked the relaxed attitudes of the non-equity theatres I've work for. If there are issues, things have been talked out and dealt with without having to resort to miles of contract rules and regulations. I know that I've been lucky - the things that I've been asked to do have not fallen into any category that I've not been willing to do. I have worked at an Equity theatre once - which BTW denied the Equity SM overtime when working 70+ hours in a week, and was supported by Equity in doing so -. I know that there are dozens of folks with bad non-eq histories for my good non-eq history.
I just have a hard time with all the nit-picky rules. I've seen really simple situations turned into complex contract negotiations. Right now I'm at a theatre which is taking a $150 dispute on a union (IATSE) bill and turning it into a multiple hundreds of dollars 'your lawyer needs to talk to our lawyer' because both sides have their own 'interpretation' of what the contract says/means.
Its definitely a situtation where you need to work around the enviroment to see if it's one that's going to suite your personality. There's nothing wrong with union environments - but they are very, very structured and controled. For the kinds of shows that are typically union (Broadway, huge musicals, large-scale tours, etc.) that kind of draconian control is needed. What you need to think about is what kind of shows are you interested in? I'm a very hands-on kind of person, and enjoy helping out whereever there is a need. I spent years working on small-scale children's theatre because I liked the fact that if the set broke, I fixed it, if a costume tore - I sewed it. To me the challenge of stretching my abilities in whatever direction was needed is what I enjoy, and I like the hands-on do-it-myself. At a union theatre, there's going to be much more sitting-behind-a-desk, don't touch anything yourself, lots of rules and regulations that control every part of your day (which, when you live in that environment, do become second nature - that's part of what working in an equity environment before becoming equity gives you, that second sense of when its break time, overtime, etc.)
I could go on and on, I was never able to figure out if I wanted to try going equity full time, and took that hesitation to mean that I shouldn't pursue that path. I'm lucky - I have a SM job now that has good health care, retirement benefits, comp vacation time that I earn when I work over 40hrs in a week. Those are few and far between when you're not equity.
-Centaura