Your hair is really healthy looking, so if you decide to transition, at least you are starting at a healthy point!
When I was fully relaxed, I used to rollerset my hair anyway, so as I started my transition, I continued to rollerset and just flat iron my roots, then I would wrap my rollerset for my hair to be straight.
Before I wrapped my mind around transitioning to natural, I had already done a 6 month stretch, so I knew I could do it. If I wasn't rollersetting my hair, I was doing a flat twistout. (did rollersets more though)
As I got further on and the NG starting taking over, I started to do a lot of co-washing and bunning. Most people don't like to bun, but I really like the sleek look of a bun. Some of my staples are Tressemmee conditioner, Giovanni Direct Leave In, and coconut oil. I stopped using shampoo a long time ago (it wrecked havoc on my already tangled hair) but once I started to really take my time and detangle my hair with a lot of conditioner, it was smooth sailing. As my transition progressed, it was difficult to wear my hair straight because of the contrast in the thickness of my NG and how the thin relaxed ends looked in comparison. After about a year, I no longer wore it straight but would let the stylist curl each section with the flat iron as he straightened it. I used one jumbo flexi rod to maintain the curls (like in my avitar). But I only went to the salon every few months to get relaxed ends cut off.
I hope that helps, but if you have more questions, please feel free to ask.