Welcome to Sailwave.
Answering Q2 first - yes you can take your current Sailwave.BLW files from a PC to a Mac and there are several ways that can be done: Dropbox, pCloud, Google Drive, Microsoft OneDrive or old fashioned sneaker net aka memory stick.
Q1 - if your purchase of a MacBook Pro is new and therefore comes with the latest version of MacOS ‘Catalina’ you will need to purchase Crossover for Mac to allow Sailwave to run. There is no native version of Sailwave for Apple Mac systems. Others have successfully run Sailwave using Crossover.
Previous versions of MacOS could run WINE and therefore Sailwave would run, but Apple have removed the 32-bit infrastructure required from ‘Catalina’.
Neither Jon or I have access to Apple Mac systems so our help will be limited.