I have pondered this lifestyle for many a year and by all means it's appealing as it gets.

Funding is main hurdle, given one is fortunate enough to have the recourses to liquidate, rent or invest. Finding where to invest is the question. Doing the sums on how much your going to need to do things comfortably and safely depends on the individual/s and the level of comfort you can live with for an extended period. Lets say 30K GBP (50K US) per annum ? That's 82 quid ($136 US) a day, will it be enough for everything? Depending where you are you'd have to invest over a million to get the returns, from a bank anyway.

Visas are a big hurdle, for instance 3 months in Europe, for non residents will fly by (trust me just been the and done that) and you cant get back in for another 3 months! No amount of grovelling will change the situation either!

Shipping a bike in my humble opinion is simply out of the question, time consuming, excessive paperwork not to mention damn expensive. One bike in the EU and one in the US is adequate, get the same model so you can transport the spares, tools and knowledge with you.

Health insurance, bike registration, insurance and upkeep, finding somewhere to store your bike/s, getting from one continent to the next, maintaining communications, phone, internet access ect ect will in total incur considerable expense.

A solution of sorts,

If one could afford to purchase a couple of relativity inexpensive properties and turn them into homestays, B&B's, backpackers, campgrounds or small hotels (I'm stumped for an accurate description) the benefits and rewards may well be worth the considerable effort.

For example a property in Spain and one in Central or South America, (all 3 ?) you can apply for business visas which are longer and multiple entry or permanent visas, you will have a permanent address to register and insure vehicles, accommodation and a workshop ect ect. Furthermore you may well get a reasonable return out of it and better still, be able to claim some of the expenses incurred for maintenance, upkeep, depreciation and maybe even some of the travel and bikes and consumables ect if you run tours. Given your choice of location I don't think it would be too hard to get hold of a Hubber or 2 to run the show whilst aboard either. I'm considering taking the leap and bringing a dream to fruition.