Hi Dove,
Good questions! Here is just my personal opinion.....
InsuranceI was doing lots of dangerous stuff like sea cliff climbing, etc on my trips so I grabbed a cheap safety-net health insurance policy through
Ehealthinsurance.com. That way if I had a fall or big accident, I would be covered
once I got home and my travel insurance quit. I think I'm paying like $60 a month for the insurance, which sucks, but I feel more comfortable
pushing my luck on trips.

So...its a personal decision that you have to make.
Like a lot of people. I usually use World Nomads for travel insurance...they rock hands down. Here's some info on travel insurance and
other alternatives to World Nomads:
http://www.startbackpacking.com/travel/travel-insurance/MotorcyclesI hired a motorcycle in Thailand and road all over the north through the mountains, it was one of my best memories! You can rent a scooter (which is the Asian "motorocycle") for about $5 a day or maybe less if you negotiate it for a long period...like 2 weeks. They are also extremely cheap to buy there as well, just make sure you get paperwork for VAT so you can get taxes straightened out when you leave. you can buy petrol in 2 litre bottles in convenient stores, fruit stands, and on the side of the road....it goes a long way!
MoneyThis is the toughest subject because there is no answer! My $20 - $30 a day in Asia covered EVERYTHING...food, transportation, entertainment, scuba even, you name it. Everyone travels differently, and the more practice you get the cheaper you can keep it it seems.
Cheers!