I need to give this serious thought and this experience may push me back to a Catalina 25, which feels way smaller and more manageable at least for now. I'm scared I could regret it and pine for the extra room and size if I ever find a lady friend, lol...
If you can afford it and it is a good as you say the size fear will go away in about a week.
So if you keep the boat for 5 years you are trading in one weeks discomfort for 259 weeks discomfort.
An I had a C25 for one summer and loved it.
There are many many reason why at c27 may not be the boat for you.
Being too big to single hand is not one of them.
Yes you will need a mate for the first dozen sails or so but you should probably have a helper for the 25 anyway.
The 27 you can stand up in.
That alone is worth a couple days discomfort until you get the hang of it.
I sailed a c30 single hand for a couple years then chartered a 34. Wow did that look big. By the second day it felt right. When I got back to the 30 it seemed tiny.
Like I said before.
The 25 is fun for overnight but the 27 you can go for a week.
In fact someone sailed around the world on a c27 that he significantly beefed up.
The potential value difference is significant.
If the po has 50k into a boat he wants 10k for compare that to standard issue 25 for 3k that you have to put 2k into to be usable and safe.
Of course the c27 will cost more for everything and if you can't do it you can't do it.
But don't pass because you are concerned about handling it.