What's the difference between "visually lossless" and real lossless and what does this mean for future encodes?
Technically lossless, or real lossless, means that when the output is decoded by a conformant decoder, the result is mathematically identical to the input.

Visually lossless is a non-rigorous term that indicates subjective transparency i.e. output which to the lay human eye looks indistinguishable from the original. The output may look different if a viewer scrutinizes it in fine detail, but not in normative viewing conditions. As to how 'visual-losslessness' is determinined: there are video quality metrics, like PSNR and SSIM, that provide a quantitative measure of the difference of an image with respect to a reference. Subjective opinion tests have been carried out to establish threshold values for these metrics that can be used to define 'visual losslessness'

From Performance Analysis of Visually Lossless Image Compression,


  Note  that  there  are  several  visual quality metrics (indices)
  such as MSSIM [6], PSNR-HVS-M  [7],  WSNR  [8]  and  some  others 
  that  are  able  to characterize  well  enough  quality  of  lossy 
  compressed images  [9].  Recently,  it  has  been  shown  for 
  grayscale images  [5]  that  it  is  enough  to  provide  MSSIM 
  values larger  than  0.985  or  PSNR-HVS-M  values  larger  than 40dB 
  in  order  to  guarantee  practically  invisibility  of distortions 
  in  lossy  compressed  images.




As for re-encoding resilience, depends on what the goal of the re-encoding is. For viewing-only or casual re-editing purposes, CRF 18 in x264 should be fine. For professional re-editing, I would drop the CRF to, say, 12 or 14. Information, once lost, can't be perfectly recovered. But you can set your own standards by encoding at different CRFs and comparing manually. See https://video.stackexchange.com/a/17639