Yikes! That's a lot of repair to have been faced with so early in the aircraft's journey, so good thing you've persevered and gotten her back into proper flying shape!
We have a tailwheel DPE (Robin) coming down to KPAO from Oregon later in August to do about 3 check rides, all in tailwheel, including my own, and then we have another tailwheel DPE named Karen who's coming out from Missouri in September and will be setting up her "check ride shop" out of Livermore!
I am also one of those guys who had taken years to do what usually takes a year or so but I have a job and a family and took large chunks of time away to do startups and other really intense things that grounded me for 3-4 years at a time. Coming back each time felt like starting over, but some things also "stuck" so it hasn't been a total backslide each time, and I used the time to also fly multiple airplanes and broaden my experience with long cross-countries, doing lots of solos through complex airspace to polish up the radio work, and so on. It annoys me that my check ride is still pending this summer, but there's always something to work on and a check ride is just a moment in time, before which you were learning a ton and after which you'll be learning a ton - it never stops - so it's also good not to overthink it. It's not like passing a checkride instantly makes you a hot shot pilot, if anything, it just puts you in greater peril.
Keep training, would be my advice. Practice those emergencies like they're actually happening (because they *might* - I've already had one!), don't just treat them as a drill. Use the checklists to the point of absurdity because that's what the DPE will want to see, even though the Decathlon checklist is... how shall we say it ... not that complicated? Such simply airplanes lead to complacency on going methodically step by step, however, and the DPE is going to want to see that you have the discipline such that when you later transition to something more complicated, you won't have a "jump in and go" attitude.
Where are you based,
@yetiking ?