If I don't get in on round one I'd finish my undergrad and spend my last year getting A's and beefing up my EC's. If I need to re-take the MCAT again after studying for it DIFFERENTLY than I did the first time, I'd do that. Then I would apply shotgun style... just shoot at everything and hope something falls (apply to like 20 schools or even more). I would also apply to "special masters programs" this time, in case I don't get in again.
If I don't get anything the second time I would do a one year SMP and try a third time. If I'm able to do well it will not only boost my gpa but also prove I am fully capable of handling the rigors of medical school. From what I've read if you are dedicated enough to do a SMP and do well in it, you've got a really good shot at getting into at least one school.
Also when I apply the third time I will probably apply to a few GOOD Caribbean schools - but only the ones that have a relatively good track record of getting graduates into US residencies.
If I don't get in a third year to any MD/DO/Caribbean schools, then I would be forced to re-evaluate my career ambitions because becoming a medical doctor obviously isn't working out. I might toy with doing PA, but my real second career choice would probably be to get a PhD. Professors (once they have a spot at a school) enjoy a relatively decent lifestyle with a ton of autonomy and independence. Other than teaching classes you can basically set your own hours and even do a lot of your work from home if you want to. If you are good, the pay is decent... nothing fancy but it will take care of your family. I don't know if I would necessarily enjoy living in academia the rest of my life, but it wouldn't be too bad.
If for whatever reason NOTHING worked out - no MD/DO/Carib./PhD/PA... then I would probably abandon the medical field altogether. My next goal would be to just get a half-way decent job (don't know what field) where I could get some experience... and maybe after a few years getting an MBA.
Man this got more and more depressing to write and think about as I went further and further down the list... I know there are people who would apply 4 or 5 or however many times it took until they got it, but for me there would come a point where reality hits and just providing a steady income any way I can for my family becomes more important than "fulfilling my dreams" of becoming a doctor.
That being said, unless you are at that point already and don't have time to keep trying, anybody who not only wants it bad enough but is willing to work hard enough to get good grades and prove their competence, whether it be as an undergrad or as a returning grad student, has a high chance of getting accepted somewhere.