There are alot of options specialy in Dili, all along the beach side you find people seling cars. You can make direct looking and negotiation.
You can also visit some of the local dealer in the Main protocol road, CityAuto and few showroom selling new and second hand car, good quality and also less than 5y old. Goverment only allow shops to import 5y olds vehicles.
On beach side,you may find cars older than in the car showroom.
We have insurance company INTL and sinarmas both offers car assurance.
Normally buying a vehicles is easy, the seller will help to do all the paper works, dealing with authorities for changing of ownership, just give gew dollars 30$ or 50$.
Ownership changing cost is 25$ and it takes a week or so. But original documents will be collected in 2 or 3 months time.