Thank you both for the responses, I really appreciate your feedback.

Whilst I don't own any property in the UK, I am renting one out, and have the tenancy agreement documentation to prove it. I also have a long running record of always returning to the UK after visiting the US. (I've made several earlier and much shorter trips around 2010-2012) I will also have return tickets for both the flight in question, and for the train home in the UK. I should also note that I have never once overstayed, and I always spend more time out of the US than in it. (despite those recent lengthy visits, which I kinda regret now lol)

Regarding taking a file with me, I typically do for every visit just in case due to my habit of over-worrying! I've never needed it before in the past, other than showing my return ticket to the last officer I met. I'm hoping I won't need it this time either, but I will definitely make sure to prepare one. Thanks for the tip.

I really feel I should've waited until next year to visit again, but like I said.. I've been really real stressed/burnt-out as of late and really wanted a vacation, so I figured I'd go visit one of my other best US friends. The funny and ironic thing is, the thought of getting dragged off into secondary and possibly refused entry is causing me even more stress and anxiety than before I'd booked everything! lol

Sorry if it sounds like I'm worrying way too much. I really am trying to get myself excited over seeing Chicago next month, but the thought of being bounced by CBP is really getting to me. My own fault sadly for reading up on various CBP horror stories on the internet, heh.