Thought I'd share answers to questions I received via PM:
I have a couple of questions (while dreaming if this could become a reality for me) that I was hoping that you can help me out on:
1) What line of work were you and your wife in that allowed you to take 3 week RV trips in the past? I imagine that I would need to do short trips to make sure my family enjoy's them. My job though would probably allow me to do 1-2 weeks max at a time and that is assuming that I save up all my vacation.
I worked as a computer programmer. I received 4 weeks of vacation per year, which I carefully hoarded. We didn't get sick days, so it did mean going to work sick a few times to keep all my days off so we could do our trips. It also meant working on Chol Hamoed, which was unfortunate, though our 2012 trip was over Sukkos so that worked out.
2) How do you finance all the costs while RVing long term? Is it from savings, rentals, business or none of your business 
Our house was legally converted into a duplex a few years ago. Rent from the house makes up most of our income. Since we hardly ever pay for camping (see the Camping Chart menu item on the blog), our primary costs are food and fuel. Thanks to Obamacare, we get very cheap healthcare since our income level is considered low enough to get significant aid.
3) How do you manage with kosher food on the trips where there isn't much available? Do you simply know where all the kosher areas are and stock up in between?
Trader Joes nationwide stock chicken and ground beef! We call ahead to make sure they have it in stock. We can fit 16 pounds of ground beef and 20 trays of boneless chicken in our freezer, which lasts about two months for us. Other than Shabbos, we have meat a couple times a week.
Kraft string cheese is now kosher, which has been amazing for us. The reality is that we have to be in a community on a monthly basis anyway, so we can stock up then.
4) For a newbie RV family would you recommend starting out with a newer but smaller pop-up style RV or a older more substantial RV?
If you already own a fullsize SUV or Van, I would buy something like what we started the trip with, the Wildwood XLite 26XLBH. It was $11K new, and sleeps a lot of people. What's your family size? That makes a big difference.
I would avoid motorhomes, as they can't be serviced everywhere. I like to separate my engine from my house, so each can be replaced independently.
Compared to a conventional travel trailer, Fifth-Wheels are amazingly easy to tow and much easier to hitch up and disconnect. The limited passaenger capacity of a pickup truck won't work for those with more than 3 kids.
