Jewish Law question - What if you can't take off work on Jewish holidays?

A Ba'al Teshuva friend of mine approached me a month or so ago and told me that they really needed to talk about something.  They started a new job after a long period of unemployment and did not have any vacation or personal days yet.  He said that he didn't believe that he would get fired if he took off all 6 of the Yuntuf's this year, but he was living hand to mouth and simply couldn't afford the loss.

Before I state my response, let me preface it with saying that I'm not a Rabbi.  Even though I've been learning for 10 years or so, I'm not nearly qualfied to render any final decisions on Jewish law. 

I told this friend the same thing and he told me that he didnt have anyone he felt comfortabel asking. 

Since I was forced to tell him something, I took the following principles into effect:
1. Life and death: If someone really is in a situation where they're life is in jeopardy, then most Jewish laws are suspended if necessary to save the life.  Example: A person is trapped on a desert island, on the brink of starvation and comes across a bacon double cheese burger.  The person should eat it without hesitation.  Once he's on the rescue ship, it's a different story.

2. Torah laws, Traditional laws, Rabbinic laws, Customs & Stringency: A simple explanation is as follows:
A. Torah Law: G-d said the "though shalt" or the "though shalt not" right in the Torah
B. Traditional Law: We have a tradition that Moses taught the law orally at Mount Sinai or in the desert.
C. Rabbinic Law: Decrees from our sages
D. Customs: Something that the Jewish people took on without being told.
E. Stringency: Going beyond the letter of the law in service of G-d.
These are listed from most important to lease important.  The importance in this situation is that the 2nd day of Succas and Simchas Torah are both Rabbinic decrees, while the 1st & last days of Succas along with Rosh Hashannah are commandments straight from the Torah.

3. 2 steps forward, 1 step back... or 1 step forwards & 2 steps back
Just like when exercising, there's a potential for someone to push themselves too hard, injure themselves and have to sit on the sidelines for a while, the same can happen spiritually.  Those of us who spend time among Ba'al Teshuvas have typically seen at least one case, where someone was eager to learn, took on a lot very quickly and ended up spiritually melting down and walking away from Judaism.  This is a definite concern and needs to be in the mind of every Rabbi or spiritual advisor.  If I push this guy guy to do something that he's simply not spiritually ready for, it may send him into overload.

4. Degrees of violation
Maybe there's a way that he can sleep at someones house near his work and walk to work to avoid the problems involved with traveling on a Jewish holiday.

All that being said, I basically explained my thoughts on all 4 of these areas and let him make up his own mind.  I never asked what he ended up doing and he never told me.  As I was walking away, he asked me what I would do.  I told him that I hope and I pray that I'm never tested with such a difficult problem, but I'd like to think that I would take off work and trust in G-d to take care of his end of the deal.