The issue I see is with medications. Insurance only allows you so much at a time. So if you put 3-4 days worth in each vehicle, you don't have enough to get you through the month.
And, as your medications change, you have to remember to change out all the various "go bags".
Instead, I recommend getting a small container to carry your must have meds and keep it in your pocket or purse with your keys and wallet. Then regardless of where you are or how you got there, you have the meds. Carry 4 days worth - that is most always enough time to get your insurance/doctor/pharmacy to get you a refill.
With the container, you can easily change out with new RXs, etc. And you are only putting 4 days aside rather than 4 days for 2-5 vehicles.
Also, remember that most Rx insurances don't cover stolen meds, so if your vehicle is stolen, etc, you will have to pay for those meds out of pocket and wait for reimbursement from your car or home insurance. As some meds are really expensive, it can cost you.
Most Rx insurances have a "vacation request" allowing you to refill before time once or twice a year because you won't be able to fill while you're away. When my home was burglarized, they stole ALL my medications. I was able to use my yearly allowance of vacation requests to get enough meds to put me back on track with their automatic timing of refills. You can also use this to fill your Rxs if you are stuck somewhere without your pills. You only pay your usual copay. But you are limited as to how many times you can do a vacation request per year.
1975 American Clipper RV with Dodge 360 (photo in profile)
1998 American Clipper Fold n Roll Folding Trailer
Both born in Morgan Hill, CA to Irv Perch (Daddy of the Aristocrat trailers)