Hi GGearon,
Inplace upgrade: No, not from 2008R2 to 2012R2, you have to do a fresh install, best solution in any case. The 2 cases I talked about was impossibly lucky cases i have heard off, out of ~60 cases.
The best scenario is to build 2 new servers.
1. 2012 R2
1. 2016 or 2019
Inbetween of the 2008R2 and 2012R2, is the 2012, you dont need to do the jump to that, because the JET DB was not upgrades that much, but it was highly changes in the 2016 platform, hence the "jump" step from 2012R2 to 2016 or 2019, depending on what OS version you are aiming at.
Again:
Comming form below 2012 R2, then you have to do a clean install on a 2012R2 and then from there either inplace or fresh install to the next version you like, so far it is possible to go directly to 2019 from 2012R2 but not from below this version.