Hi All - what a great site and resource HU is - only been here a few weeks and already have learned heaps

I am seeking any advice (particularly from those who have done similar) on a couple of options that I'm looking at for a trip we're just starting to plan for two years time

The wife and I want to ride old Route 66, both riding

Figure we'll take 3 weeks or so

From Melbourne, Australia we're looking to fly into Chicago, couple days looking around; 2-3 weeks exploring the mother road; then a couple days with friends in LA and fly home again

Initial research has told me that to hire a couple Harleys will cost me around $7k US - pretty expensive

Another thought is to fly our bikes into the US, ride then sea freight home. The thought behind air there is to avoid any customs delays which are quite regular from what I'm told (customs delays in Melb when we're back aren't going to be a big issue); but from research it looks like air-freight bikes into the US is quite difficult these days

OR - buy bikes in the US and then sell at the end of the trip, or ship home. Initial thoughts are its lot of hassle for 3-4 weeks but may be an option....

Sea freighting home is not a worry as my mate in LA has freighted stuff to Melb when he was back and forth between countries so can help on that end. Also have a local contact in Colorado

So - to the questions:

Has anyone done the Route 66 road trip with hire bikes? Cost, companies to use, tips, tricks etc?
Has anyone from Australia flown their bike to the US? Cost, who did you use, tips etc?
Any things to be aware of when buying bikes in the US (apart from the obvious issues around bike condition etc) - transferring ownership, registration & insurance etc?

We've done a US trip with the family driving across multi-states a few years back so not stresses about the actual riding or trip location planning, its just the hire v ship v buy question that I'm mainly struggling with initially

Any help or advice gratefully accepted

pete