I need serious landscaping tips

I do not have a green thumb, I have a terrible time keeping plants alive and the mere thought of weeding makes me cringe. That said, the landscaping is freaking ugly as all hell and I need help. I love daisies. I'm thinking Heirloom Daisies, Black Eyed Susans, Cosmo's, and Mexican Daisies.....basically I'm thinking, they're pretty, they reseed every year, and they will grow tall enough that I won't have to weed meticulously.
I'm thinking of also doing a small "container garden" in some of my painted pots on the front steps / porch. Mainly just basil, mint, sage, and I want to plant a tomato cause I'm pretty sure I'll get tossed out of Jersey if I don't grow my own tomatoes, plus, I love a good tomato & basil sandwich in the summer, mmm I'm getting hungry just thinking about it. I get a decent 50/50 blend of shade/sun.
So, yeah. There is also the issue of the two ugliest tree's available being planted in my front yard already. They're two pine tree's, ugly misshapen sporatic goofy looking things. I think I'm just going to chainsaw them babies down and plan stuff over it. I'd thought of doing 2 lilacs or a butterfly bush, hydrangias or something....but I don't know. I don't want to take on too much haha.

Then I have two little flower boxes that I bought on sale at the end of the year last year @ Joanns. Once the tree's are down from the front yard I'm going to attach the boxes to the railings. I'm at a loss as to what to plant in the boxes cause I feel like they should be shorter than daisies. Geraniums, maybe Zinias, or impatients?

Also, obviously I'm on an artist's budget here, so I gotta keep it tight. This may sound like the dumbest question ever, but does stuff really grow from seeds if I just go out and plant seeds, or will it be a huge waste of time? Like, what do I do? Do I have to like single plant each and every one or can I just sprinkle them around and hose it down? I told you, I'm a complete idiot with trying to keep plants around. The only plant that I've been able to keep alive for real is a bamboo my friend Julie gave me a few years ago, and even there I suppose it's only because Bamboo is an invasive species and it pretty much refuses to die. Would it be unreasonable to expect a full grown flower if I planted the seeds this weekend or next? I have no clue! Educate me!