I start saving for my trip as soon as i get back from the previous one.
my job actually gives me 4 weeks vacation. i was suppose to get another 3 weeks for my 5 year sabbatical but due to the merger, we are getting screwed and they are not giving that to us now. Im sure the upper execs will be benefiting from it.
I use to work as an Engineer so i had all of the responsibilities associated with that title and job. Now I'm a technician, hourly wage, making as much (less) $$$ as an engineer and less responsibility. I can now leave my job and someone else is responsible to do it. I dont get calls 24/7 like i did when as an engineer either.
As far as the other things, its just a matter of details.
As far as "online booking", so far I've not had any issues. One issue i had this year was that i was trying to reserve a hotel room 6+ months ahead using my credit card. it wouldn't work. The reason. because when i was to arrive and stay, the expiration date of my credit card would have been expired. I would have (and now have) a new card - same number - different exp date. probably some Microsoft software bug. So i just moved onto place choice #2.
I do some leatherwork/repairs for a local shop. Thats about the only thing outside of my life that will need attention. But what i do about that is to give them a stop/start dates of when i won't accept anymore work and when i will start up again.
if that "project" can get done sooner than later, i would opt for the sooner and out from under it. No need to have it waiting for you to get back home. at least that is how I'm wired.
Your priorities are your priorities and only you can set them. If you want to travel more often, no one is stopping you. Only you can say NO or YES and its up to you.
just an for your info. Im a single guy and many people are surprised I'm not married. The way i see it, if i was married, i doubt i would be traveling as much since the Significant Other would be an issue. If the SO liked to travel, then it would be a +, but I'm not at that point now, so i can do as i please, when i please.
good luck and happy trails.