I'm looking at long-term index funds like VOO and VTI, but I'm paralyzed by the current price levels. Should I really care about short-term dips, or am I just missing out by sitting on cash? Is consistent investing and proper allocation better than waiting for the perfect entry point?

I am working in a small company that offers a health plan that costs $452/month, which is too much for me. I am single, healthy, and can't afford this much. And I guess there is no open enrollment right now, and I need to visit the PCP within the next 2-3 months. Are there any affordable options available for me?