Almost everywhere in this industry segment, you'll be self-employed, and therefore, responsible for your own health insurance. Regarding that, why not get coverage from the VA? Or are there family members that you have to cover? If that's the case, then you can buy it yourself. There are several places, like ehealthinsurance.com that you can research rates and buy through.
When people here talk about leasing, in most cases, they mean leasing the vehicle that you own to a carrier.
As DaveKC said in the other post, read, read read. You're asking questions, and that's wise - keep asking. However, he also (and you said,too) that you're jumping in way too fast. There are lots of folks that do well in vans & sprinters. There are tons more that fail. From what I read, vans are super-saturated in the industry (read=there's too many of them).
Here's a couple of suggestions: Since you have a Class A, why not learn driving someone else's straight truck for a bit? You already have the qualifications, and your learning curve will be on someone else's dime. You could research carriers first, then pursue driving a fleet owner's truck for a bit, learning freight lanes and the business before dumping tons of money, or worse, be a slave to payments while you make mistakes in your new-ness (and you WILL make mistakes).
If you're at Bliss, why not take a trip to the Flying J in Anthony, or the Love's or Petro in El Paso, and approach a van or straight truck driver and pick their brains? A word of caution, though: If their curtains are drawn, or their windows are covered-up, they're probably asleep-let them rest.
Lastly, keep asking questions.