I can not help you with timing, details or anything like that but I do have one suggestion that helps me manage all the meds I take. I have organized my meds into 5 groups or 5 times of day that I take them. I keep two of those weekly pill compartments. One I keep by the bed and one in my kitchen. In the keeper by the bed I put everything I need to take immediately, among them my thyroid pill, because it needs to be taken first thing in the AM, approximately an hour before I inject any proteins. I also keep in that container by the bed the meds I need to take at bed time. When I organize for the week, I take those bedside bedtime pills first for that first night. That way, when I wake up in the AM, whether I immediately get out of bed or not, I have the meds I need to take immediately sitting in the compartment for that morning and nothing else. To explain a little better I put the pills together for the week on Wednesday night. At that time I take the Wednesday night meds out from the Thursday pocket, which leaves the Thursday AM pills in the Thursday pocket. So I can literally take those pills without even turning on the light, because I took the evening bedtime pills out the night prior, with the light on.

Then the rest of my meds I spread across three times during the day and keep them all together in a large day organizer, one for each day of the week. When I get into the kitchen and start fixing something to drink, I take out the pills for the day, separate out the first round and put the mid day and after dinner meds back in.

If you have to space things out into say 5 events or more, keeping a pill organizer by the bed for those first and last to take might help you out. I certainly understand this being a concern, It's maddening to me when I miss a pill or lose track of time and take something late. Being sick is like having a full time job some days and we shouldn't have to feel that way.
Best of luck, Sylvai