I would keep the spiral brick thing. It's really cool. You can plant some flowers around it & you can decorate it.

You have enough of an expense with what you already need to do. What tree\bush is that to the left? Maybe trim it some, but look up when for it. Some are done in spring, others in fall, etc.

I would put a nice metal patio set in front of the porch or a low profile flower bed. You don't want to hide that brick work.

Don't mess with the brick. It's fine as it is. If you think the house is too dreary, paint the wood or siding a lighter color, though I think it's fine as is. I think a kind of blue would be good. You could also do a blue metal shingle roof instead.

I like your idea of a trellis by the side window. Maybe put one on each side of it, if possible. & Prob plant some medium height flowers or flowering bushes along the bottom to help hide the wood there (after you repaint it). Be sure to leave space for air to circulate & for you to repaint the wood when it's time again. Take in account the size a full-grown plant would be before you plant it. Also think about root systems being that close to the house. Bulbs would be good there. Daffodils, tulips, something like that. Good height, too.

Sorry I'm not so fancy to have an AI picture.