When you ask these questions of four people, you will probably get six opinions....
I have both worked at and been a recreational navigator all my life. So, when I plan an excursion, I always start by planning it in detail. That plan is sometimes good as long as the third day and sometimes not.
First, If you aren't traveling for some reason and on a hard schedule, making reservations more than three days (maybe even two) will be a waste of time.
Second, if you don't currently have a laptop with a planning (like S&T or SA) program, get one now and start learning to use it. There are overlays available with all kinds of valuable information.
If you don't have a smartphone, make plans to get wire (web access) at pretty regular intervals so you can get weather, fuel prices and such. You can use the travel plan to make stops at McD, Panera, BK, and coffee places that are known to have WiFi. Also get an Alfa long range Wifi. You only need this if you can't connect with the phone.
It sounds like you have a lot to learn. Learning it all at once may be painful. Things like the Post Office will only hold mail for 30 days. How are you going to pay you bills in that two months?
Do not let any of this dissuade you. If you do at least start, you will never have a road life.
Matt - most of my road life has been on water