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I'm a 5'7" guy with a morning weight of 270 lbs (yeah, I know) I don't want to get too specific and dox myself.

I have three questions that I will provide back-round for but for the impatient they are:

1. is hypertrophy important at all; or is strength king and thus the primary aim and I should let the chips fall where they may? Any truth to rep ranges dictating hypertrophy and strength?

2. Is it healthier to get to a proper body weight and then try hitting the weights again? or am I better off to fast while trying to gain strength in the weight room?

3. Caffeine, Creatine, Cardio: how much of each would you recommend?

I got up to damn near 300 lbs and decided to start fixing myself before it was too late. So before the holocough I started lifting weights and trying to lose weight. My weight has yo-yoed back and forth and I am just gonna commit to fasting. By day 2 of a fast I start getting cramps in my rib-cage multiple times a day. I started taking salt which seemed to help but not eliminate the problem. So I may just start alternating my fasting days. I would like to fast 3 days a week but don't know if I should be lifting on those days.

I started lifting again over a year ago now and my numbers are good (I used to lift when I was younger and it seemed to come back pretty quickly) but am having trouble figuring out my next steps in this area. I bench, squat, deadlift and row once per week. I do band assisted pullups twice per week. On the three major lifts I started by doing 5 X 5 and thought I should be aiming from muscle growth to help shed fat and started doing higher reps on everything but feel like crap doing that.

As of now I am taking a week off as I am sore as hell from going to failure on all my lifts the last couple of weeks. I want input on what I should do moving forward in the weight room while trying to lose weight. My current numbers are as follows:
Bench: don't know my max but have gotten 3 sets of 5 at 345 and have gotten one set of five at 355 (barely got 5th rep).
Squat: disproportionally weak compared to bench but I am built weird. Tried to get 435 for 3 sets of 6 before I decided to take a week off and only got 6 on first set then 5 and finally 4 on the last set.
Deadlift: I use a hex-bar with the handles up because I really suck at deadlift. so I just do the weight that I squat with and it feels easier (probably because I am basically doing rack pulls in this set up).

I have only done jump roping for cardio and have been very sporadic with it. Should I do lighter weights for more reps while I try and lose weight while increasing cardio? I feel like I shouldn't be getting over-trained since I am only doing the major lifts once per week but have been fatigued much more than I figured I should be. I am middle age so that might be part of it.

Before I get too old to do it should I be aiming for more hypertrophy than strength in order to serve as a base to build further strength on? If so should I be going to failure with lighter weights at higher reps or is that all bro science bullshit? Should I just focus on trying to maintain strength for the next six months while I focus on losing weight? My weight has gone up and down while I have been trying to accomplish both at the same time, so maybe I need to shift focus instead.

If any of you guys fast, do you do it while lifting on those days? I have tried and it seemed okay but don't know if I am shooting myself in the foot in the long term.

Any insight is appreciated.