@Retro6 Thanks for keeping us updated and it's good to hear that you've been having fun and are making some changes.
A couple of things to add:
Clothes. Getting some new togs is a great idea and the opinions of a woman are also a good idea, but do remember that what she thinks looks good on you might not necessarily chime with other women. Also, you need to feel comfortable too, so don't get drawn into wearing something you really don't like. Do some research on the sort of clothes that flatter your body type etc. On future dates if you're comfortable, you'll be confident.
Also with the pics I personally would avoid professional pics. Modern smartphones in good light take great pics. I totally agree that a good range of pics is great, but IMO good natural pics of you in different situations and activities would be fine and portray an active man who can scrub up when he needs to, but doesn't need to polish a turd.