Spec builder version slap together version of "Craftsman". Bad marriage of newel posts at top of stair. Go right ahead and paint in an "almost black" . Not going to be fun at the base of the white spindles. BM Kendall Charcoal would work. I see no paint sin here. Sorry. Someone ran to Home Depot........................: ( for that "turned" post, which is there and not square...why?? Because it would have had to have been custom.. Paint sinners unite lol , the "muddle" is already in place and no harm done with paint at all.

Is the house located in the PNW? Looks like it could be in any one of various older Seattle neighborhoods....very typical style :-) If that is the case, maybe look for some regional input. Don't do anything with the rock wall....that is also extremely typical to the setting and the cost to replace would be exorbitant!! Generally, these boulder/rock retaining walls are filled with a variety of low maintenance, easy care evergreen rockery plants that bloom in spring in a variety of colors. Weeds there tend to be a non-issue unless neglected for months on end. You just need to thoroughly clean out any weeds from the planting beds (NO weed and feed - that is only for lawns and is highly discouraged here due to pollution) and add low growing broadleaved evergreen shrubs and/or groundcovers. These will be the lowest maintenance garden enhancements and you are not short of dozens of possibilities for this area. All local nurseries will carry a wide selection and year round. If not including groundcovers, mulch to keep weeds to a minimum and use a pre-emergent like Preen to reduce their occurrence even further. I don't understand where the new proposed hardscaping/bike storage shed is to be or where the second set of steps are. Can you post photos that illustrate these?

Pictures?

Message the conpany and they will send some