Welcome back. Will keep you in our prayers. Let me give you a few suggestions to try.
I think the number one thing that I have found correlates to success is what amounts to a different way of thinking.
A LCer can not abide a sweet tooth. IMO we have to treat sweets much the same way as an alcoholic treats booze. I love ice cream and I thought the LC ice cream was just the greatest thing but after several half gallons vaporized in a flash I realized that I must avoid the sustitute products and train myself to eat naturally low carb and not feed my desires. As Job made a covenant with his eyes not to look on a woman to lust over her I had to make a covenant with my tongue regarding starches and sweets. We can not afford to say I can't live without [X].
You are going to have to be more strict than some because of the diabetes and change of life issues but you can beat this thing. Be patient with yourself.
Here are my specific recommendations
1. Oil of Oregano drops to be sure that your GI tract is clean and functioning well.
2. Coconut oil for overall GI health also
3. Calcium, Magnesium and Vitamin D especially in the winter time.
4. Use lots of Cinnamon in cooking (or take capsules) for Blood Sugar control. Do not use it to make sweet treats though.

5. Make sure that you get enough saturated animal fat and protien.
6. Zero trans fats... none. Also avoid Polys.
7. No grains, sweets of any kind or starchy veggies for at least 3 months.
8. No processed foods or substitute products (bars, shakes, Ice cream, LC breads or tortillas etc.).
9. Make good use of the kohls (cabage, broccoli etc).
10. Make allowance for female issues. Don't beat yourself up.
11. Fish oil. Baked Salmon (YUM!!!)
12. Remember some medications make weight loss much harder so your progress may be slower than you like but progress is progress.
Now regarding finances
http://www.daveramsey.com/ Find a station that plays his show and drop by the library to get a copy of his books. Mr. E has referenced one of his bits of advice and I can personally attest to the efficacy of his common sense approach.
Blessings to you. mike