Navigating Insurances - Health, Life & Disability

I'm having difficulty navigating different insurance options provided by my employer and third parties.  I've gotten Life Insurance coverage through my employer up to the max allowable without a health questionnaire or medical exam (which I would most certainly fail with Stage 4 PSC, mild UC and taking 5 prescriptions/19 pills per day).  But I'm unsure if it would make a difference if I tried to get additional life insurance through a third party.

Additionally, I'm having the same challenge with Long-term Disability coverage.  I have the max allowable through my employer without having to do a health questionnaire or medical exam, but that only covers 50% of my income for up to 10 years of being disabled.  God forbid this disease renders me permanently disabled.  I have researched some third parties for LTD coverage, too, but their health questionnaires are so lengthy that I'm sure I wouldn't be insurable. 

Plus, I'm concerned if I were to apply for life/LTD/additional health coverage and get denied that I would be "black-listed" with all providers, sort of like when you have bad credit, anyone that pulls your credit report knows about it.

I certainly don't want to leave my family unable to make ends meet if anything happens to me, but I don't know if I have any additional avenues to pursue.  Does anyone have any advice?