I'm 65 in November and have selected a supplemental G plan and Part D.
For me, the "discounts" on Supplemental plans made them difficult to compare by price. This will probably be different by state. My state does not allow attained age pricing, so we have application age or community rated prices. But for community rated pricing there is typically a discount for buying "early". In other words it costs less if you are younger. OK.
The discount is usually in the fine print, difficult to find, but it's on the order of 30%+ at age 65, so very significant. And the price comparison sites just give the discounted price without mentioning that it will be going up. Typically the discount decreases by 3% (of the full price) each year for 10 or 11 years. A built-in price increase.
And then there's the problems noted in other threads here about how the insurance companies will change plan features, costs, or enrollment, or create new insurance companies for the same reason. So it's really hard to make a decision about the value of any supplement plan. And if I want to switch plans in the future I will probably have to go through an underwriting process and pay at a higher new application age rate. Time will tell if I've made a decent choice.
Plan D didn't feel quite as bad. I'm on four prescriptions, all generic. I was able to check on plan costs at medicare.gov, though the cost presentation was confusing, particularly when looking at a partial year of coverage. And while you can compare costs for drugs you currently take or may take, there's no easy way to know if a plan's formulary is otherwise reasonably comprehensive or value priced if you need new drugs in the coming year.
Most plans have "preferred" pharmacies. You need to select the preferred pharmacy in order to get the lowest costs. So more searching for each particular plan's best prices, before comparisons to other pharmacies. There was only one drug plan that covered all my prescriptions within the first two pricing tiers.
In addition, I had to be a little careful to get my prices before the deductible was satisfied. If everything remains stable I won't be exceeding the deductible during a year, so co-pays are not necessarily important to me at this time. I was able to find a drug plan that promises to cost me less for drugs, at a nearby pharmacy, than I currently pay at Costco. And the premium price change for 2020 was nominal. That's nice, but formularies and tiers can change, along with prescriptions and premiums, so who knows if things will go as well as I hope?
The one good thing for drug plans is that there is no underwriting, so you can change plans yearly if you want. Seems like a lot of us will be doing that for 2020. A poor plan selection can be fixed the next year.