With regard to medical insurance, step one would be to look at your state’s insurance marketplace website. People mistakenly believe that these sites are only for people who qualify for subsidies under the ACA. They’re not — you can definitely buy unsubsidized individual plans through a state marketplace. This will give you a rough idea of the premium costs in what is (in many places) a competitive market.
For any plan you’re looking at, get a copy of the plan’s Statement Of Benefits And Coverage document. This document lays out costs for a variety of medical claims. The beauty of it is that the questions it asks are standardized so you can compare apples to apples.
Individual plans on the marketplaces are rated on a platinum/gold/silver/bronze scale based on the plan’s actuarial value — the percentage of your expected health care costs that are covered by your premiums vs. the percentage covered by cost share (i.e., copay, deductibles, and coinsurance). Basically, the idea is to assess your own risk of major health problems — if you’re super-healthy and you only see your doctor for a checkup and a flu shot in an average year, a bronze plan will save you money, but the downside risk is considerable if you get cancer or get hit by a car. You can minimize those risks by getting a gold or platinum plan, but at the expense of higher payments every month.
HMO vs. PPO is for most people a cost vs convenience consideration. PPO plans don’t require you to get a referral from your primary care doctor to see a specialist (usually not a big hassle in my experience) and usually let you see out of network providers (which is valuable if you travel a lot but otherwise not worth the extra hassle and expense.)
If a plan has a deductible (most semi-affordable individual plans do) you should assume that ANY medical care you receive will be paid for out of pocket until that deductible is met. (You should also assume that your doctor has next to no idea what any one procedure will cost you out of pocket.)
If you’re looking to save money on premiums you should look at narrow network plans. You give up even more freedom to choose your doctor and hospital BUT it can save you considerable money vs plans that give you access to almost everyone.
If you have assets to put aside, definitely look at creating a Health Savings Account, which lets you save pre-tax dollars in an investment account (similar to an IRA) with the catch that you can only spend that money on health expenses.