All the flowers that you planned to water

A plea for help:

I'm sure I've mentioned my scary jungle of an overgrown yard. It's so overgrown it's daunting. Overwhelming. Every other year or so I go out and prune the snot out of a bunch of bushes, getting crazy satisfaction out of my ability to make things look different.

But it turns out 80% of what I've whacked has been bushes that spring back around the cuts with 6 new, fast growing shoots. So I have, essentially, made things worse in the long run.

Anyway, we know of a young man, eldest son of a homeschooling family, looking for outdoor work this summer. He is more than willing to take on taming our yard. BUT ...

I am not sure how to go about it. I mean, he's not a landscaper, I can't just turn him loose without instructions.

And I don't know how to make a plan, much less carry one out. I have a few bushes and plants I want to keep. Between them are bulbs that I wouldn't mind keeping, and feel bad hurrying, but am not sure how to locate, especially when they've been squelched out by more aggressive plants.

My three main questions are:

how much is worth trying to save? Is it worth trying to dig up medium sized plants that I don't hate, much less the ones I invested in because I liked, to escape being annihilated? To ... what, replant in a more orderly fashion? We are thinking it's time to essentially start over, rather than sentence this young man to a lifetime of weeding; to bury it all in weed block fabric and mulch.

how do we *plant* things if we go the weed barrier route? do we cut holes and stick plants in? And is that foolish if I have no *big picture* plan of where my landscaping is headed?

And what about bulbs -- I would like 1.) an ocean of early spring bulbs and 2.) some plants that look reasonable most of the spring/summer/fall. Big perennials I can see growing thru holes in the weed barrier, but bulbs can't really work that way, right? 3.) low maintenance is a must

I like the cottage garden look but not sure I could pull it off, I think it might take more work than it looks.

I am tired of aggressive plants that look pretty for maybe a week but look weedy before and after blooming, like my rampant foxglove.

And, like I said, I'm hiring a young man willing to do outside work, but not a landscaper ... I think maybe he'd be willing to dig holes and plant if I knew what I wanted where, maybe ... but maybe I'm not being realistic.

I was going to post a picture of my overgrown space but can't find one. I know they're on my space somewhere.

Oh. here's one from 2 years ago:

it looks similar now, maybe a little more overgrown.

Here's what some agressive pruning & mowing did, also 2 years ago:

That's the front of our house, btw -- there's no door or window hidden by that bush, the "front" door is over on the left side, facing the driveway. It's weird.
Any thoughts are appreciated.