1. How high and when do you think the price will peak at during the current market cycle, meaning before the next 2014/2015 or 2018 type bear market?
$25k - $30k is the closest and more realistic figure in this current market cycle before the worst bear cycle that you have described occurs, which will most likely happen on late 2021 or 2022.
Another bullish predictions is the $100k mark and it was considered as "possible", but not really possible in this current situation and market movements/sentiments.
2. What is your selling plan for any long term bitcoin you are holding? Gradual selling? A single sell target - what is it? Just gonna see how things play out? Or maybe you plan on holding more long term and don't even plan on taking advantage of the market cycle.
Gradual selling. Sell at a realistic target range of $25k-$30k (depends on how Btc is working it's way up when it reaches beyond $25k. If Btc struggles to reach the $30k, I might be selling in the middle of this range.)
While the other fractions would be sold on a more bullish perspective. Say like beyond $50k-ish to $100k maybe on a span of 5 years or so.