The Story Special comes to mind...that's what Pete was flying at the time he designed the Fly Baby.With landing gear acting as anchor to flying wires, shocks would be a challenge. Breaks though should not be a problem. Flybabies have a similar set up- breaks but no shocks beyond the tires. That said, I am not convinced you need shocks. I am sure Ron W has thoughts to share on this.
You could of course also perhaps deepen the fuselage a little and attach the landing wires to the bottom of the fuselage as opposed to the landing gear allowing for a simple wittman style gear. The loads in the landing wires and compression in the spar will be higher but nothing that cannot be handled/engineered. Much simpler than a cantilever and maintains the period wire braced look.Of course, another option would be to design a cantilever wing or a single-strutted wing like Souricette and eliminate the struts and wires to the lower pylon altogether. That would make it easier to have both a retro version and a more modern enclosed version.
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Here is a nice pic and drawing of the Ryan gear, it does seem like a simplified version could be done with a leading (not trailing) link gear on a pair of rigid tripods that also anchor the bracing wires or struts. Rubber disks in compression or even scooter suspension parts might work as a lighter, simpler, and cheaper alternative to oleos. Of course, at this point it almost seems like I should go with a low wing for a more 1930s vibe to the design, but not many side-by-side, open-cockpit monoplanes come to mind.
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I was describing a light two-seater so more like a European two-seat microlight or an American LSA at the lighter end of the spectrum.If you plan on approximating FAR 103, you'll have no need for mechanical suspension or spring gear. The weight penalty is excessive. Decent sized tires at 10 to 12 psi will be all you need. Don't overdo it on the tires, though, because those fabulously in vogue bush tires eat up a lot of horsepower.
Leading links like the Ryan ST and others make more sense if you figure the bracing at about 25% chord and the main gear forward of that point in a taildragger, but I think that starts getting more complex than I’d really prefer. The Farman sprung straight axle and spreaders or rigid gear like a MiniMax seem like better solutions for a simple build.What about something like the Wilga, rigid legs with trailing links.