I would chime in on what @big_greg said. I also own a MHDT Labs Orchid R2R DAC. I had upgrades done to it by grannyring. Total invested in the DAC is about $1500.
Here's something to consider. I did an extended shootout on a very high quality and sensitive system with the Holo May vs. Orchid. Holo May has somewhat smoother highs, more presence in bass and midrange, and a wider, more articulate soundstage. But not by much. Maybe 5-10%. And this was in a very resolving system.
My host also had a Holo Spring 3 DAC. In his view, it gets "90% of the way" to the Holo May. So, personally, if I felt the urge to upgrade past my $1500 modded out Orchid, the Holo Spring might be the way to go. It would help hedge the risk factor of repair -- though it seems that Tim at Kitsune is already providing that hedge.
Oh, and I have heard MHDT's Jiun is very good to deal with.
In a nutshell, you've got good options, and I think the risk is a bit less than perhaps you are supposing. My two cents.