Hey, Ellie Look at how well loved you are! Lots of good advice here, and I know you will figure something out.
This all reminds me of the kinds of struggles STBX and I would have about money...and in our case I was the one doing the bookeeping because yes, I am much better at it. What you said about your H feeling that "he makes plenty of $$ and should be able to buy whatever he wants" is my H to a "T".
For us it was a control issue. H felt that he made "most" of the money and thus he had a right to spend it. The way we solved it was to have the shared account and then we each had our own separate account that we didn't have to report to the other one about. I don't know if something like that would work in your case, and it probably wouldn't be a solution to the immediate problem of your H wanting to get in on the Baja condo, but maybe this will simmer down and you can implement something similar.
Also, I hear you about wanting to be less dependant. I would say that is the best outcome of my own situation...although I have worked our entire marriage I never made enough money to fully support myself...but that is changing!
It seems to me that you would be a natural teacher... Would you be able to make enough teaching at the Med School?
There is no way you can be the loving supportive wife and mother that you have been, and that your family is used to if you have to work full time. Your kids will only be at home a few more years...is there any chance you could start something part time and then transition to full time when the time comes? (and you will have 3 kids in college!)
You have had a very full plate the last few years...I can't imagine you dealing effectively with your D and all those issues if you were juggling a job on top of that. Just bop your H upside the head for me one time!
wishing you all the best, SG
Survival Goddess "The most common way people give up their power is by thinking they don't have any." -Alice Walker