2. Two existing machines have the same IP address* (I am guessing a static IP somewhere), it will mess things up so change it if you want both machines on the same network at the same time.
*I am guessing this includes subnet.
3. Firewalls are the same on any OS that matters. I would look at a hardware one though.
4. If security is your concern I would not hard encode wine into the system (it is fairly easy to get puppy linux to stick "wine" in front of the command line to launch exe files). Remember it is ` (left of the 1 button) to launch a command line window from file viewers and tab autocompletes a line (nice for the mixed case file names windows app like to sport on occasion).
3. N/A
4. I mean you can essentially get linux to autolaunch windows apps in the same way it does linux apps (a single click). WINE does not tend to wind itself into the system as much as it could (if a virus deletes your "program files" directory made by WINE (I forget where it is and you can even change it) it would not be half as painful as it could be for the same thing to happen in windows) but giving autolaunch with WINE abilities to exe files can help things spread if you are not careful.
Also remember all users are root on puppy linux (most people do not even make a new user and stick with root user and the stock password of puppy) so any damage can be magnified for the "right" malware compared to other distributions (most of them) that use limited user accounts.
5.n/a
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btw i feel this a good time to remind you guys that sea of thieves was made by rare, who also made DKC1-3 and DK64, alongside banjo kazooie and conker's bad fur day