I did something similar but only over a three-year period.
I bought my
current boat in
Croatia and spent the first summer cruising there, wintering in Dubrovnik.
The following summer we went down to the
Ionian, cruised there for a couple of months and wintered the boat
on the hard in Preveza.
The following Spring I moved the boat to Catania and in the summer cruised
Sicily and southern Sardinia before coming to final home port, Menorca.
The good part is we got to cruise distant places breaking-up the long trip over the three years. We could not have done that if we had to come back to the home port at the end of every cruise.
What can be difficult is finding the places to winter, someone to look after the boat and performing the inevitable maintenance work.
Our boat was a bit complicated (wooden, almost 50 years old, recently bought) so this made it harder.
If the boat you buy is easier to look after and winter
on the hard it might be OK.
How long do you plan to cruise for in the summers? If it is only 2 or 3 weeks I would recommend chartering. If it is 2 or 3 months then
buying is probably a better option.