We live in Queens, near the Woodhaven Blvd LIE exit, and have driven down 4 times, though the last time was in December 2015.
1. What time do you leave home?
We usually aimed to be fully loaded into the car and ready to pull out between 5:30 and 6am. On a weekend, that is early enough that the drive through the Midtown Tunnel/midtown/Lincoln Tunnel is traffic free enough that it beats going all around the Belt and through Staten Island. Adjust according to your specific location on LI.
That is not early enough to avoid DC traffic, but we never wanted to get up in the middle of the night to start an all day drive and that's what you need to do to beat DC rush hour, even on a weekend. We often took a bypass down the Crain Highway a bit east of DC in Maryland [Route or Highway 301]. I think we usually got to that from 695 around Baltimore, to 97 to 301. It links back to I-95 around Richmond. But we also found that area got more developed over just the 3-4 years we drove it and ended up getting backed up there as well. Hard to say what's the best of mostly poor options. Check your favorite GPS/MAP planner for your best judgment on that.
2. Do you drive straight through or make a stop If you stop overnight where?
We usually eat dinner somewhere in NC, and try to push on to Santee, SC for the overnight stop. You can also overnight on Florence, SC which is an hour closer to New York. Santee leaves you ~6 hours from WDW, Florence, about 7.
3. What time do you leave WDW for your return home?
4. Do you drive straight through or make a stop If you stop overnight where?
Coming home, we usually leave not quite so early, probably between 7 and 8am. We overnight in Rocky Mount, NC. In our experience, there are, frankly, no ideal or even good options for passing through or around DC and approaching NYC on the return trip. The Crain Highway again is a possibility, but seems to work less often than going south. You especially can never leave early enough that you won't hit traffic returning to the NYC metro area. I suppose you could time it to hit your first bridge or tunnel some time between 1am and 5am, but we've never had the stomach for that sort of trip timing.
Also, coming home, traffic can be rough until you hit I-16 near Savannah and lots of people peel off to head towards Atlanta and assorted Central Time Zone locations. Then it usually clears up, but can slow again when you hit SC where I-95 narrows to 2 lanes.
5. Do you think it is safe to drive?
6. Do you think I am crazy?
Sharp answers Yes, then No.
Longer answers: I'm not sure if you mean generally traffic and relative transportation safety or Covid related issues. On general safety, I believe flying is usually safer than driving, but that does not make driving unsafe. We have never had an issue or even found any stretch of road between metro NYC and Orlando to be particularly dangerous or filled with crazy rage drivers or anything like that. As for Covid, that's really a matter of personal comfort level I think. I would not hesitate to drive to FLorida right now based on safety. Of course, everything entails some risk. Even staying at home.
Crazy? Goodness no. It's not everyone's preference,but I think it is definitely worth trying once. We've never done the all day no stop option, though it can work. It's just not for us. In all, we try to do 60-70% of the driving on day one in each direction, and leave less for day 2, in both directions. We also find stopping for meals is refreshing enough that it justifies the time it takes. My wife and I always split the driving. It's both fun and tiresome. Unless you're certain you'll hate it I say go for it. You might never want to do it again, but I think you'll probably be glad for the experience.
