Here are some pics

I like transitions in doorways, I don’t like transitions in openings. Openings with transitions make me wonder if there had been a wall that was removed. And since yours looks more doorway than opening, I’d put a transition. But this really is a case of there is no wrong answer.

A continuos flow of flooring always looks best. Avoid break ups/transitions as much as possible, unless you need it functionally.

Flooring manufacturers will state maximum run before requiring transiition pieces. Read the instruction and technical data sheet, before starting. Every manufacturer is different. Different construction and material has different requirements.

Ok. Since we are novice, would it be a safer option to use the transition?

I’m thinking that if it’s the slightest bit off (the walls are very unsquare) at the start, we could correct anything at the transition. If we run it continuously, the error … just continues. What was 1mm at the start could be a while cm by the end.

Does that make sense?

*whole

It will look worst if, you break it up. A continuos floor will look straight compared to two separate rooms with floors going different directions.

You can start from where your longest run is located. Then work out from there.