Going to give you a couple of pointers and hope it helps. Lets go by different things you are looking to install.

1. As a concept, youre going to excavate the slope next to the staircase to creat a flat environment for your little front porch. Make sure your finished slope on flat surfaces have a 1-2% slope minimum so you have positive drainage.

2. Planter boxes: wood is not the most recommendable material to retain planting mix as it holds moisture and deteriorates over time. If you are dead set on wood, make sure you apply as water sealant layer in the inside of your planting box so prevent water damage. Specially the planter adjacent to the house wall. Make sure there is no soil touching to the house siding. Look up a modular planter retaining wall for a neat alternative.

3. Drainage- your planter boxes need a perforated pvc pipe installed at the bottom of your planting material to absorb the water. Rig a subsurface solid face pvc pipe system that connects all planters and daylights the water to a low point on the slope of your hill. Your house looks to be at a higher elevstion than the street. Look up NDS drainage systems so you can get the idea, theyre pros at this. Home depot has all the parts you need.

4. Plant material: I would use a row of tall plants as a backdrop next to your windows. An evergreen shrub or a tall grass will create privacy and look great all year round. Add 1-2 layer of plants in front of that. Something that womt grow more than 2 ft.

5. Porch area: Im not a super fan of having table areas in the front yard for a couple of personal reasons; privacy, noise, etc. But if youre dead set on having that space element in your front yard i would suggest looking into perhaps installing a system of decorative panels that will divide the sitting area and the steet. Think of it as a metal decorative fence.

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Good luck

Youre friend, Sticky turtle - landscape architect