Questions regarding TransAmerica cycling route and preparation

[staehpj1]

There's not just health issues there are logistics too.
All solvable, I'm sure, but requiring pretty precise planning and prep.

Precise planning and preparation is not always necessary. Even 22 years ago I was able to get my health insurer to cover a three-month supply of my daily blood thinner "up front."  Took one phone call to explain that I would be travelling and may not always have convenient access to a large pharmacy chain. These days, obtaining a 90 supply of a maintenance drug is quite normal.

Yeah, most insurers will allow 90 day refills.  I know it is the default for mail refills with mine for maintenance drugs if by mail.  There still may be issues with drugs that require special storage conditions like refrigeration or at least avoiding extreme temperatures.  This is more likely to be true if you need injection type medications.  It can be worked out but it may be less simple.  I know that my wife's medication has pretty stringent requirements that would require some logistical planning.

[Barak10]

Thank you all for your advice and insight. Regarding the medication issue, it does require some planning. However, I have done my share of research to complement the advice I received and am confident that I know how to resolve the issues and plan properly.