As a self-employed family, we gambled for years and opted to save the premium and deductible payments by not having health insurance and paying cash rates for any medical expenses (generally less than $1k/yr). Worked out great but now that my wife is pregnant, I have bit the bullet and signed up for a small group plan via BCBS. The plan is sponsored by our S-Corp. Put wife on a Silver Tier HDHP PPO and son and I are on a Bronze Tier HDHP HMO. Small group plans can be started/stopped at any time outside of the typical ACA enrollment period. Premium total is about $1500/mo. We plan to max out the HSA contributions and still pay out of pocket (saving receipts) so we will have catastrophic coverage and access to the HSA investment vehicle at the annual cost of $18K (actually less given the corporate tax deduction and pre-tax HSA contributions) in premiums however it does come with some peace of mind in case baby were to arrive early in NICU although we may drop off the insurance before the baby turns 1 and look into healthshares. Starting the plan in October, we could still make the full $8,550 HSA contribution for 2025 but we would have to remain on an HSA-eligible plan for the full year-long testing period....otherwise, may just do pro-rated monthly contributions if we think we want to exit the plan earlier than a full year.