To start a separate subthread.
Assuming for the moment that the Roadster idea is real.
When might this idea have happened?
He's had the roadster since around 2008, so that's no constraint.
In 2016, there the professed intention to launch Red Dragon to mars in 2018, though this seems to have slipped to 2020 by May 2017.
By at the latest summer 2017, it was clear Red Dragon was not happening.
The launch windows for Mars are roughly every two years:
Oct 2015-Mar 2016
Oct 2017-May 2018.
Nov 2019-Aug 2020
Up to March 2016, it's clear that Red Dragon was thought to be the first payload to Mars, and at this time it was clear that F9H wasn't in any way going to be ready for the trailing edge of the 2016 window.
As late as May 2017, noises were being made about a dual Red Dragon in 2020.
It seems unlikely any concrete development would be made on the Tesla plan before it became clear that NASA wasn't going to fund RD, and the decisions about retro-propulsion on commercial crew killed last hopes of doing it without NASA funding, as it would have been yet more investment at a time when ITS/BFR was coming into mind as the way forward.
For several of the proposed inaugural Falcon Heavy launch dates, it would have entirely missed the window to Mars.
In April 2017, it seemed that FH might make the october beginning of the launch window, if everything went right.
So, if up till July (?) it was thought that Red Dragon was happening, it may be that they had to initially aim at design and construction for this payload to happen in 3 months or so?
Perhaps by April 2017 it became clearer to Elon that Red Dragon was not going to proceed, hence the 'silliest thing we can imagine' tweet was aimed at this idea, meaning ~6mo.