John,
I understand the need to crawl before you can walk, but I also understand that a major illness can wipe a family out, financially.
You might look into some sort of cafeteria plan, where the corporation offers a variety of options and sets a payment level that it will contribute towards those options. This could result in employee co-pays in some, or perhaps all instances, but it would be better than nothing. Even if the employees had to pay 100% of the cost, I expect that the corporation can get a lower rate than an individual can on their own. This would at least offer some benefit to the employees who, after all, are what will make this railroad survive and prosper.
I don't know tax law, but you might even be able to make a year end corporate contribution to the plan, depending on year end profits. The post on TSA's may offer some possible avenues to investigate as well.
Good luck.
Michael Allen