(1) Those with two free Roadsters, will probably get them 24 months apart.
That makes sense for several reasons, including minimizing the tax burden on the winners.
(2) Tesla will only allow the Roadsters to be registered in the winners name.
Unlikely. Tesla can't actually enforce this if I want to register the car in the name of my business/LLC. Then after purchase, the LLC members can be changed/transferred without incurring a resale event or sales tax.
(3) You will owe 1/3 of the FMV of the Roadster as Gift Tax, payable to the feds and state the quarter after you pick up your car. The law allows a portion of gift tax over $5000 to be collected at time of transfer of the gift to you, so Tesla could have you show up with a check for 25%, and the rest you'll need your tax accountant to figure out the remaining federal and state tax liability by the end of the next quarter. Hypothetically, a $250K car with 9.75% sales tax in California will bring the total to $275K (excluding title, registration, any applicable luxury or gas tax, etc...). So 25% of that is $70K for the feds. Yearly registration to get the sticker will start around $2100 as well according to the CA DMV site.
That's not how the taxes on the awards work. It's not a "gift" and gift taxes are not part of this. The award is treated as regular income, and Tesla will just send you a 1099-misc at the end of the year for the FMV of the car. It's up to you to report that on your tax return and pay the tax at your regular tax bracket (although you may owe quarterly estimated taxes if you are not in a safe-harbor from the previous year). Of course, if you have a $250k income boost that year due to the Roadster, you'll be in one of the top income tax brackets. For 2022, that's s 24% of the amount over $172,750 for married/joint filers. There will not be any kind of income tax collected at the time of award transfer (other than sales tax).
(4) Tesla may offer a cash value at 50% of the FMV that could be used for another Tesla vehicle of their choice if they choose not to get the Roadster due to the huge gift tax liability. The cash value is also a gift as well, so that will be taxed accordingly.
Again, it's not a gift. It's regular, ordinary income reported on a 1099-misc. See above. What would be nice (but also unlikely) is that Tesla offers a gross-up to help winners pay the income taxes. I won an award from Amex several years back worth >$5k and Amex sent me a check for the taxes on that award. Of course that itself is taxable. There's a simple formula to calculate tax gross-ups for awards like this. In my case, the check Amex sent was more than the actual taxes I had to pay, so bonus.
(5) They may stagger referral winners with those who purchase a Roadster so they aren't flooding the secondary market with referrals winners telling their Roadster for a reduced price.
That would be nice, but it would have to be a really slow rollout to make a difference. There's still going to be plenty of NGR award cars for sale just so the winners can pay the tax on the award. And you think it's going to be a reduced price? I'm thinking the first group of Founders NGR award cars will sell for a significant premium. Unique color(s) and "Perceived scarcity".
(6) We still don't know if the Space X package will be part of founders edition.
Definitely won't be included (IMO). Tesla will certainly try to upsell award winners on this.
(7) By the time Roadster configuration occurs, I suspect the FSD package to be upwards of $20 to$25K, and to be an extra optional add-on to the Roadster (even for Referral Winners).
This is a toss-up, could go either way.