Samoht, you mentioned that Diana was getting hardly any opportunities. I've had several self-employed sims, and that has been a problem for all of them. Two things I've done are to have them take part in community events, like the Amateur Olympics and the Eating Contest; and with my painter, I had him work in a rabbit-hole job for a week to get a couple of opportunities, then he quit. If you're starting with a gardener, you might consider having her work as a scientist for a little while. Her gardening skill will stand her in good stead there, and then you shouldn't have to worry about opportunities later.
Also, for making friends, two of my Immortals/Immortals-to-be have the charisma skill, and two don't have any charisma. It helps a lot, but in my experience, if you have the Observant and Never Dull LTRs, you can make friends very quickly without charisma.