I've lived on East and West Coast in the US, visited most states and the places you mention in Canada, and I just moved from Washington to Maryland.

Realize that everything you listed as a preference is the same for millions of people. Lots of people like paddle boarding, nature, and the cities you are looking at, so those places are going to be expensive. Without knowing more about your acute needs to move I can only give general advice.

First, don't move without a job lined up or at least a plan in place. Look at college towns including in more states than you listed. They are more liberal on average, and have a baked in supply of people looking for roommates. Even older grad students are looking for roommates and are often quiet.

After that, look for things to minimize costs like public transit. You say south of Maryland, but that covers a whole lot including places with pretty bad public transit.

When you do move make sure you have any vehicle titles or purchase documents as you will need them to get new titles and registration. Update your insurance policy with your new address. Make sure you have your birth certificate, social security cards, and photo id so you can get a place to live and get your new state id. Make sure you know what it costs to do all of that (likely hundreds on the title, registration, new id). Even more if you don't have one of the necessary documents and you have to pay a notary to send a form to get a new title mailed to you.

Look at room mate apps or sites to potentially vet a low cost place you can move into more quickly than getting your own place and going through the credit checks and down payments for a lease.

And look at your credit to make sure you don't move just to find that you won't clear the checks they will perform.

Open a bank account at a bank or credit union with branches where you are moving to, or at least part of a no-fee ATM network. E.g., I can get cash from my credit union account without any fees from 7-11 and they are everywhere.

Make sure you have a few blank checks on your wallet for oddball expenses or deposits that don't take cards or have fees to do so. Have a little cash as well.

Once you have a job planned, costs figured out, make a spreadsheet. MAKE A SPREADSHEET! You do not want to move across the country to find that you didn't factor state income tax or vehicle registration costs and suddenly can't make rent. Include all likely costs and see if your budget has some wiggle for miscalculations and other issues.

Make a spreadsheet of all the tasks you need to do. Keep track of them because the details of moving will screw you hard if you don't mind them.

The more money you have while moving, the better you can solve problems. Hard truth for life in general.

If the above sounds overwhelming, then you need to plan all the more carefully.

Make sure you don't make unrealistic assumptions about the culture of where you are moving and get taken advantage of our targeted for violence. Even in the most liberal places there are places and people unfriendly to LGBTQ people. Don't be a victim.

Best of luck and happy to answer questions about specific cities, I've been to many.