If you wait for it to feel comfortable, you'll never do it.
Another way of saying that is: You are not obliged to feel comfortable before you start out.
Sometimes, if I'm trying to break out of a rut, or trying to overcome some hesitation that I don't really believe is valid, it helps me to (1) make a list of every reason not to do the thing, and (2) look at every one of those reasons thoroughly and unflinchingly. Are there any real concerns? If yes, address them. If no, grab your ear and pull yourself out the door.
For example, in your case, maybe -- just speculating -- you might give your tenants some warning of a rent hike, hire a property manager, get your vehicle a good trip check, take a self-defense class, get a better roadside-assistance plan -- whatever addresses any "real" worries you might have. If you're like me, you may go through that list three (or 300) times. Then once you've addressed each item, just give yourself permission to go.
I find that sometimes the things that seem like the biggest barriers actually take five minutes to fix, and some things that I barely gave thought to turn out to be big problems. You never really know till you sit down and stare the little gremlins in the eye.
The hardest part of any trip for me -- even the most happily anticipated ones -- is from my front door to the parking lot.
