Letting him cry was just not working. I found other conversations online that described him pretty well, they were all about high needs babies aka velcro babies. They all said that crying of any form seems to just not work with these kind of children because they will protest until their need is met, which happens to be you holding them. I took that into consideration because it really wasn't working and long bouts of him being upset only made for rough nights and him upsetting his reflux more. So we ended up doing a few things some of which I took from your suggestions and some of which we just kinda felt out.
I still nurse on demand but this is typical now.
8-830 am : Up for the day. Breakfast soon after.
1120 : Nurse
1130-12 : Nap (usually an hour and half). He usually heads to the stairs to tell me he is ready for a nap and he self settles easy for this one now. He also sleeps in his crib. Lunch upon waking.
330 : Nurse
4 : afternoon nap in his own crib (an hour and a half but sometimes two if he's been super active that day) starting to settle better for this one but still adjusting. This time of day the house is pretty active so we are trying to add more quiet time.
5 : dinner
730: Nurse and Reflux meds (we increased it to max dosage now and give it to him a little earlier than we were to ensure it was starting to work before he laid down)
8-830 : Nurse rock and sing lay him down for bed.
Bed time we are still breaking a few rules but it seems to be working. I rock and nurse him to sleep but I usually bounce him awake a little moving him into bed. We put him down in our bed (SAFELY) which seems to be working well because if he does stir he puts himself back to sleep with no complaints. Typically he doesn't wake until we come to bed but even then thats only if we are a little to noisy coming to bed. I just move him to the center away from both of us and he sleeps pretty soundly until 4 am when he wakes for a normal nurse and change then back down till 6 am. He wakes then for a change typically then back out till 8 am. He is about the same as my daughter at 6 months other than he isn't sleeping in his crib at night. I am going to be tackling that shortly. Now that he is caught up on sleep finally and we have an actual and realistic schedule I am ready to try the hardest part.
I need to type more but I have to get off here. I will post an update in a few days to let you know how the crib is going.