I can't specifically answer your questions but I do note that Hamish CEO came on in 2016 and seems to be righting the ship. But in righting it, he needs the capital so its reasonable to give him a chance. If you are buying into iCar then now is probably the right time and it seems the share price has bottomed out unless there is bad news on the horizon.
What I saw in the CR prospectus interested me as it appeared part of the CR money would be going to growing their income sources by offering insurances, car servicing etc as well as their core car sales. Also the CR is offered only through a 1 to 5.8 share purchase plan (you can only buy 1 for every 5.8 you own). Capture Group and Carsales remain the biggest shareholders in the company. The purchase price for new each new share is 18c which is the current share price and it is offer with an option share for 18 months at price of 0.20.
They say they will reach profitability in some countries by Q4 2018 and across all countries in Q4 2019 so their timeline is reasonable. It just really depends on their ability to execute. To date iCar have a bad history of raises and have not lived up to their commitments. I would say they have one or two more chances before the market abandons them so now is the time to get it right.
If they do get it right then there should be significant upside. I bought more at 0.18 and will probably take up my quota in the CR at 0.18 as well but DYOR if you plan to come onboard. You can pick up some cheaper shares at around 0.17 to 0.175 which I have seen recently.