Hi there Antie
You'll see I have split your post to a new thread - it just makes it easier to track the individual questions if any readers need to look back in a thread for information they may accidentally confuse the 2 babies which can confuse the advice you are given.
It's really fine to follow LOs lead on portion sizes. Yes you don't want the milk intake to drop significantly, I think you would know if it dropped based on how full/drained you feel and how many minutes feeding, it sounds like you know your baby well
So long as the milk continues at regular, predictable intervals throughout the day at a reasonable amount it is ok to offer your LO more than 1-2 tsp. My DS is petite, took very little milk, but loved solids. His milk intake did not drop when I introduced solids but he took pretty big portions of solids (certainly not 1-2 tsp, he would have kicked off big time if that's all I'd given him). I was cautious to monitor his milk intake of course but it continued as it had been previously (actually he took a bit more in the early days of solids so that was a big surprise) so I let him eat solids to his fill and watched his body language for signs that he was full - in fact mine self fed so it was easy to know he was finished.
Some LOs do take to solids very quickly and with great enthusiasm regardless of their size, and some take a few months of tastes before they decide to go for a full meal, it is very individual.
Yes I would suggest when you introduce a second meal to keep it in the earlier hours, it gives more time in the day for them to digest and for any reaction to show before BT. There is no hurry to move to 2 meals but so long as all else is well it is fine to offer. You might want to offer finger foods as one of the meals, sounds like he would likely enjoy self feeding
Either top off with BM or offer water, it is your choice and doesn't matter which, the top off is a thirst quencher rather than a full meal of breast milk, it is great if he likes to use the sippy cup and have water.
You asked about 'limiting factors' - there is a (shortish) list of foods to avoid before age 1yo, and foods to limit, I assume you know these (salt, sugar, honey, and such). The only other thing to watch for is the poo. It will certainly change with the introduction of solids, not like BM poo at all, and it will be more effort for LO to push it out, they do need to learn to have a good push at this stage so this is another reason not to hurry too quickly with lots of solids. LO may appear to be struggling as they put their whole body into the pushing and this does not necessarily mean there is a constipation problem, but do watch out for the general poo situation. If it gets on the harder side maybe try a prune (those soft seedless ready to eat ones are nice) before it gets too hard. Some LOs (like my DS) can become a bit constipated with too much carrot for instance so I always balanced it out with a prune or if he got a bit too soft in his poo I made sure to offer carrots that day.
It sounds like you are going to have an enjoyable weaning journey - it was one of the loveliest parts of my DS getting that little bit older, I really enjoyed watching him eating
hope this helps
Do shout out if you have more questions