Simon was running out and in many times a day as long as the weather was fine. First of all we had our food pattern. He would come in to every meal if he was already out. This was 6 in the morning, 17 in the evening, and 21:30 in the evening. If he instead of being out had been in, he would eat at the same times, and then as long as the weather was OK, run out after his meal.
In the morning if he had been in all night, he would likely only take a few bites and then run out for a while and do his inspection round and his nature needs, before coming in and finish the morning meal completely and then relax together with me. In the same way at 17, if he had been in all day, he was likely to first step out and look at the weather, then go back in and take a few bites, and then rush out on his inspection round and nature needs, before returning in and finishing his meal and relaxing together with me. The 21:30 meal was different, he were likely in good weather to just go in and eat, and then go out for the night immediately after. And in bad weather, he would go in and eat, and then go to bed at same time as I did.
On top of this food pattern was his will to be close to me, and if Pernille was out, to be close to her. So he would rush in and out. If I were not in the living room and he wanted in, he would place himself close to his boxwood bush outside the kitchen, and wait for me to see him. Or if I were in the garage or in the work room, go to the door or window outside there and meow. If I heard him, I would go and let him in. If I did not hear him, I had the habit to look for him every time I was in the kitchen. And if the weather was bad, not only to look at his boxwood bush, but also to the covers he used close to the kitchen window and front door. If he was outside, I would look at him until he saw me. If he did meow in response to seeing me, I went and let him in through the door. If he did not, I would just go on with what I was doing until a later check.
If he came in, he would follow me in the house. After a while, he would want to go out again, and the whole chain sort of restarted.