Your message would be better in another forum I think. Thus the lack of response.
For that money you don't get a lot. My advice: buy three small bikes of around 250cc where you are in south CA. This size is plenty big enough for C.Am. Get road-trail style bikes. Plenty around. If you are new to bikes then maybe use the communities page here to find willing helpers for the purchase.
As they don't use much fuel, running costs will be small. Give them all a change of filters, oil, and new tyres, and you should be okay. No guarantees though. Local mechanics will be able to get them going in case of breakdown (which can't be said of big high end motorcycles). Remember you will need helmets, jackets, boots and gloves too. Extra border payments for the machines will be required. It all adds up - not as cheap as hitching.
As for hassle, it is amazing just how pleasant people in Mexico are. Elsewhere too. Don't give it another thought.
Timescale is up to you.
One last word of warning - you'll love it so much, you'll not want to travel in any other way. So beware.
Simon
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Simon Kennedy
Around the world 2000-2004, on a 1993 Honda Transalp
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