Strip the bottom at first opportunity after haulout this Fall - perhaps even haul a bit early. You will still have a few nice days to get it done. If you can afford to have it soda blasted or dry ice blasted and you can find someone to do it then go that route. Save the manual labour for the barrier coat and new paint application etc...
I stripped the bottom of a 26 foot boat one Fall in four very long days with no help. Used a paint scraper as described - the sanding is just not practical and a lot slower. Then in the Spring do the rebuild of your barrier coat any fairing and painting. VC 17 is supposed to be launched within 30 days of application so will set your schedule. If salt water consider VC Offshore. However remember that both of these bottom paints require frequent scrubbing - if not planning to do that stick with an ablative - perhaps Micron CSC or something similar.
My best advice is to do the strip first before you tackle your other winterizing projects inside and on deck. The stripping takes the most work and is what you want to do while nice weather and crew is available. Do the interior and other work later when you are solo ...
BTW - also stripped our current 27 foot boat - also with scrapers - it is not at all fun .... process can be viewed at Complete Bottom Job
The boat had Micron CSC ablative paint over a barrier coat when we bought it and now has VC Offshore over Interprotect 2000 barrier coat
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