Depends a lot on what kind of paint is on the plane.
If it is Butyrate dope, Randolph makes a rejuvenator product that goes right on the old dope. Gets rid of a lot of cracks.
There is a similar product for Poly-Tone finishes, too.
If the plane has PolyTone, the finish might be removed by the PolyTone reducer. There is no problem with taking the finish off down to the fabric and redoing it, as the various components (PolyBrush and PolyTone) are designed to work together in this manner. This is often done for patches. How well this works for larger surfaces is questionable.
If the tail is Ceconite with Nitrate dope initial layer with Butyrate dope over that, then you would have a whole different set of problems. As I understand it, nitrate adheres to the fabric well, but not to Butyrate. Butyrate adheres to the Nitrate well, but not directly to fabric. Therefore, Nitrate is used for the initial layers directly to the fabric, then Butyrate goes on top of the Nitrate.
The problem is that you have to get down to the bare fabric using Butyrate reducer, as Nitrate Reducer does not work well on the Butyrate outer layers. When you are done, you are left with some Butyrate residue in the fabric voids. This is not good when the new Nitrate layer is applied to the old fabric - you have spotty adhesion problems.
This is not usually a problem when applying patches, but may not do well on larger surfaces.
I did this technique with the Randolph process on my Cruisemaster tail surfaces for my project. Initially, it looked pretty good but eventually, just sitting in the workshop, I had blisters pop up and wound up recovering the tail feathers.
Dave