Prior to getting married, thanks to the wonder of direct deposit and the ability to pay my Amex bill over the phone, I was able to work for months with no problem while keeping the bills paid. You can get your bank or in some cases credit card company to pay all of your bills for you, plus a lot of utilities can draft the money right out of your account (you’ll want to arrange it so that these institutions only have access to a limited amount of your money, but most banks can set up putting a fixed amount in a certain account per month and putting the rest in another… you get my drift). My bank still has banking by phone services which is great in an emergency if you don’t have internet access, but nowadays using the internet for banking is common. I wouldn’t trust a GF with handling your money, no offense against anybody’s GF but I’ve heard too many horror stories over the years. You can also hire an accountant or bookkeeper to manage your affairs for you when you are gone, and I’ve heard that can work quite well for some people and if you shop around it isn’t all that expensive. Plus they can do your taxes for you, and print out neatly organized financial reports to let you know where your money is going.
If you intend to stay single for any length of time, you might consider a condo. There are plenty of good deals to be had right now, but be careful, you can be hit with fees and assessments without warning. The great virtue of a condo is that you own the place, your neighbors probably own their places and so will help keep an eye on things, there is inherent security to the premises in most all cases (unoccupied houses inevitably get burgled), and you can even rent your condo out by the week when you’re gone if you get a condo in a desirable area.
On the car front, if you’re going to work in the GoM, you should consider getting something expendable for work transportation since it will be parked in a vulnerable area during hurricane season. If you’re going to be out for a while, either disconnect your battery or invest in a high quality solar trickle charger (the one that won’t overcharge your battery until it explodes) that plugs into your cigarette lighter / 12 v output. Bear in mind that some imports like Nissan and Infiniti do not have 12 v power with the key off, so you’ll have to connect a trickle charger directly to your battery in that case.