Hey, Huntreddog, welcome back.

I was reminded of some good work I did with my therapist; she taught me the difference between love and like; she asked me to name someone I liked, and I named my husband. She then had me give her 3 words to describe why I like him and I replied, "He's warm, fun, and friendly". She then had me apply those to the people I love/my family. . . My stepmother was not any of those and only one of my 3 brothers mustered up.a

We should just hang with people we enjoy hanging with! Our friends we get to choose, we don't get to choose family. No reason to feel guilty that some people are chosen as friends and others aren't and thus no reason to feel guilty for not hanging with family or others that we don't like! Yeah, if your family were sick/dying you'd go try to help if you could, pay your respects, but they don't have anything really to do with "you" and what you are trying to accomplish.

I don't know about your therapist; if you don't like her age (most therapists are not just in it for the money) or experience, I'd try a couple more, just to get a better sense of what is out there as far as what they have to offer; some of the ones helping with CBT/DBT might offer you some of the self-esteem work you are looking for.

I like this online book and working through it: Psychological Self-Help. Chapter 14 looks like it might be especially helpful to you?