Here are my biggest what ifs, and how I'm handling them:
What if decide we don't want to full time, and have to start over from scratch?
At the 8 month point of our journey we'll be arriving back in our home state. Forgoing any unforeseen tragedy, we should have at least a couple thousand bucks left along with our emergency fund of $2000. I figure, by the 8 month point we'll have a pretty good idea if full time van dwelling is something we want to do and can finance. If we choose to bail, it'll still be warm enough to live in the van while we find an apartment and full time jobs. Also, part of our trip will be scoping out different cities where we might want to settle down.
What if I lose my job?
On top of me working from the road being something my company has never tried before, and the fact that the company is on the verge of collapse, I could lose my job during our travels. My hope is that this doesn't happen until at least the 8 month point when we'll be at a crossroads. I'm hoping that I can manage to find enough photography work on the road to sustain us as I'd rather do that than my current job.
What if the van breaks down?
Once we have our van, one of the first things we'll do is do as much preemptive repair work as we can manage. Once we know what we're getting I can do some research into the most common repairs the vehicle might need, and get those things checked out. Anything that is even borderline we'll likely replace. I'd rather spend the money up front when we still have a house, than be stranded on the BLM land somewhere or forced to get a hotel room while repairs are being made.
These next two are pre trip What ifs that might put an end to our journey before it even starts.
What if we can't rent out our house?
Property values have gone into the toilet where we live, so it's not likely we'll be able to rent our house for high enough rent to cover our mortgage payment. To mitigate this we plan to use part of the house to store our remaining "stuff". This means renting to someone we know and trust enough to take care of our things. Even with cutting down the rent, the only friends we have that we trust enough might still not be able to rent the house.
What if we can't take our cats?
We're trying very hard to figure out a way that we can bring our two cats with us on the road without exposing them to dangerous temperatures in the vehicle. I'm pretty sure I have a handle on making that work, but I'm not 100%. There's also the chance that the cats will be opposed to the idea entirely. We plan to do some test runs over the summer to see how they manage. If it doesn't work out, I'm not sure what we'll do as one of our cats is temperamental and I wouldn't feel right passing him off onto someone else, and I couldn't bear sending either of them to the Humane Society.