Re. frost line: Since what my mason is doing is basically a dry stack wall; from here: http://www.doityourself.com/forum/lawns-landscaping-outdoor-decor/451549-frost-line-retaining-wall.html#b A dry stack wall does not matter. The joints have enough space to allow this heaving movement. The large spacious joints in a dry stack wall are like expansion joints in other strucures, they will take movement.

You need to be more specific about what it is you are wanting to do because your picture scares me. Railroad ties rot and your chimney does not look like it is attached to the ground. Hard to reach from the road? Does that mean hard for construction crews and materials to reach the lake side cliff?

I can't tell much from the photo. It looks like we might be looking diagonally at the slope. Would be better to look across it (perpendicular to the line of slope.) Also, you should explain what you're doing so I don't have to guess. It would be good for you to draw a plan view sketch of what you're doing and maybe draw a x-section sketch through it, too. How high a retaining wall are we talking about here? Often, a goal is to balance or minimize cut and fill so that you don't end up with an extreme protrusion on the land and don't have to import a lot of dirt. So you likely wouldn't bring in a bunch of dirt and build around it.

I agree with Revolutionary Gardens about a planting bed adjacent to your home. I live in Northern Illinois where our frost line can exceed 3 feet. Yours must be less based on your existing footers. DIY is a challenge doing things correctly and the time/manpower. Speak with your local “Permit Store” for building codes and also talk with a landscaping supply for best materials. Also consider disposal of excavation - you’ll have to remove topsoil, etc. to be replaced with gravel. For reference, i moved top soil to build our adjacent planting gardens, subsoil was hauled away and approximately 120,000 pounds of gravel brought in as replacement fill. It took 7 months (mostly weekends) and done with shovels and wheelbarrow - I opted mot to have heavy machinery destroy the remaining lawn. Good luck.