Shades of Green or Resort With Annual Pass Discount in May

We are planning a 10 day trip for May 2020. We have stayed at Wilderness Lodge on our regular Disney trips since it opened in 1994. My husband is retired military and we are considering staying at Shades of Green for our 10 day, adults only trip this year. They are not eligible for the Magical Express, so we are thinking about staying at a Disney resort on the first and last day of our trip. Any thoughts on this? Also, we are planning on getting an annual pass for one of us. Do they usually have annual pass discounts for May and, if so, when might I expect to see them announced?

Shades of Green is lovely, and you can’t beat the price. They partner with a transportation company, so it’s not too much to get a ride there from MCO. I’d rather pay a little for the ride than have the hassle changing resorts, but that’s just me. I know there are people who like to do that just to try out more than one resort.

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Thank you!