To bais yakov maidel:
Also, if you’re interested in more advanced, logical, and analytical hashkafa check out hashkafacircle.com
Probably different than what you’ve been exposed to.
There really are a lot of deeper and more advanced hashkafa works available but they’re not popular in Charedi circles. One of the most famous is Halachic Man by Rav Joseph Dov Soloveitchik; it’s available in English and would appeal to someone with a background in philosophy. Based on your description of what’s bothering you I would suggest reading this book – it’s available from Amazon.