I am considering upgrading from my 2006. What questions need to be asked when considering a 2014 Prime with 95K?
Prime first arrived in 2017 If it's a 2014 with a plug It's a PiP Prius Plugin. A PiP is a Gen 3 Prius and the first year for the Gen 3 Prius Plugin was 2012. A Prime is a Gen 4 Prius with a plug. the differences are quite extensive.
A 2014 Prius Plug-In (presuming that’s what you’re looking at) with 95k, is still a relatively safe bet. You’d want to get on EGR cleaning soon though. It may or may not have the revised piston rings; that happened partway through model year 2014, dependant on the VIN. The pre-revision rings are lower friction, but have proven prone to excessive oil burning. Also, and this at least is detectable with a test drive, brake booster/pump components have proven failure prone, and frequent pump cycling (whirring sound) would be evidence of pending failure. Once when first opening drivers door, then just every 10~15 minutes or so, would be normal, but every minute, or less, not normal.
The first question would be: has the head gasket already blown, and was sealer used to hide the damage?