As for buying another house, my next permanent home will likely be on a seastead or sailboat. I left the US and do not see returning unless they have a USSR moment.
Rental car will be difficult, most places I have traveled to in Europe I opt out of getting a rental and just get a hotel in the city and walk everywhere. I always book my hotel rooms through expedia which accepts Bitcoin so there's no problem there.
For things online that require a credit card, I used to rely on brawker.com but now I need to figure out a new way. Hopefully the Bitcoin community fills the vacuum that them leaving has created..
Will you be buying the boat or renting it?
If you'll buy it, aren't you at risk of being caught? what if for some reason they ask where did you get the money from to buy that boat?
That would be my biggest concern, because once they ask you.. what options do you have?
I will buy it. If Bitcoin is over $1k I will pay the guy with bitcoins. Otherwise I will sell my house and pay for it.
As for asking where I got the money...I will likely be buying the boat in a foreign country, most likely registering it under a bahamas flag. If I do pay with bitcoins I will do my darndest to pay the appropriate income taxes because I love the IRS and want to have sex with any agent reading this.