wordpress way too big for its britches: I need advice

My weblog was begun in September 2003, and I’ve been quite consistent about posting. So it’s very big. Beyond that, I started in Movable Type (oi, the miseries), and moved over to WP at about the halfway mark. I also changed service providers twice, which caused no end of trouble.

oh yeah:
(for some reason the link isn’t showing up, so here it is, plain vanilla: https://rosinalippi.com/weblog )
A good friend needed to start a weblog for her business, so I did that for her. Got WP installed, customized the theme she wanted, installed and adjusted plugins.

And now, I am so envious, I could scream. It’s like I’m living in a huge, decrepit monster of a house that is falling down around me. I’m always putting out fires. Things go zonk for no apparent reason. She’s in this sleek post modern number where everything works.

On her weblog, automatic update? A snap. Plugin update? Half a snap. Database backup? It makes me dizzy to compare it to backing up mine.

I don’t think there’s a solution, but I’m hoping somebody tells me I’m wrong. Would it be possible to start a new weblog that referenced the old one? The search function would have to search both weblogs. I know I could do that Google search, but I wouldn’t know how to handle moving people back and forth between the weblogs.

Other people out there have a lot bigger and more complex blogs than mine. How do they handle it? Can anybody give me some hints?

An example of the kind of thing that goes wrong:
I’m told there’s an update available. I hit ‘automatic’ — which I’ve done many times. Usually it is a long and frightening wait, but in the end, the update comes through. Today I tried it, and I got a ton of error messages about wrong paths. I’ve changed nothing. Not a thing. So now I have to go dig in and figure that out.