That's a lot of post. In a quick glance, after one or 2 pretty obvious errors, I gave it up.
Firstly, Luke 14:33 is not a command & certainly not a command for all of us in all times. There are some applicable points for us to consider about discipleship, here & elsewhere in our Text.
Following a Rabbi around in discipleship was not some simple matter for the masses to do. Jesus often weeded people out. He is simply telling a crowd that starts following Him (14:25) what it will take to literally & physically walk with Him as His disciples. To paraphrase a bit: Jesus had to be first priority above even family and life itself; there would be rejection, toil & suffering; you needed to prepare and make sure you can finish; you needed to be able to go through this ordeal & be victorious against odds and not soon be giving up and asking for peace. 33 is simply saying where I go, you go and you'll need to leave your stuff behind to follow Me (as some did).
Jesus did not have anything he gave up all and was provided for by God so this is how Jesus walked this is how we must walk also he said it plain and simple to be his disciple you must give up all your possessions and sell it to the poor that is plain English.
There are many calls and conditions and tests. I agree with you on the leanness - it can be very refreshing and provide for great focus to be unencumbered. The test to rely on Him and prioritize Him and what He says to prioritize, can be quite the experience. But there's more to it than you're preaching.