I had already lost my insured car that you get at the start of the game by the time I had enough money for this so needed an insured car for this achievement - This is my solution and may not work for everyone. *For reference I have the Special Edition so unsure if that makes a difference*
An easy way to get this achievement for the least outlay possible is to amass $80k and using your mobile navigate in the web app to the Dynasty 8 website (under Money and Services) and purchase the cheapest home which has a 2 car garage for $80k (The second cheapest is $87k). Once you have finished exploring your new home, use the mobile web app and this time select Travel and Transport and go to the Legendary Motorsport website, scroll down and order the Elegy RH8 car which is free if you have joined RockStar Social Club
, with built in tracker and insurance, and the achievement will pop.
If you vote negative please leave a comment on why so that I can improve this solution. Thanks
[EDIT] Thanks to GoGoJesseyo for pointing out the Elegy RH8 is free if your gamertag is linked to RockStar Social Club
[EDIT 2] a quick guide to making money :
Boost cars and sell at Los Santos Customs - best prices are for SUVs (does not accept luxury cars) Can only be done once per day in game (approx 45 mins real time)
Collect the cars Simeon asks you to find (wait till he texts and follow instructions)
Hold up stores
Mug AI people (lurking at ATMs is good for this)
Kill other players and steal their money
Race other people online
Complete missions/jobs that people ask you to do
Play on the stock market (Buy low sell high!)
[EDIT 3] For those who have played GTA Online during October 2013
R* is depositing $500,000 in online bank accounts for players to apologize for the issues that arose during the initial launch of the game - full details herehttp://www.rockstargames.com/newswire/article/51565/grand-th...