The structure of the month on the [Calendar] tab is such that only 6 rows are allocated for content, and the formulas used to return content for each day are hardwired to return just one item per formula...for the 1st, 2nd, 3rd, etc. items that meet the day-matching criteria. You happened to have selected a formula from the 4th slot on one of the days in your 1st post (that's what the "4" was for...and two rows below that was the "6" you were asking about). I think a better approach is to eliminate all of the formulas that return information from the [Content] sheet because those formulas are tedious to maintain, as each returns only one value, and even within a day mini-block, all of the formulas are different. The formulas can be upgraded with this replacement:
=ARRAYFORMULA(IFERROR(FILTER(Content!$B$6:$C$24,((A4=Content!$I$6:$I$24)+((A4>Content!$I$6:$I$24)*(A4<=Content!$J$6:$J$24)))>=1),""))
which spills all matching information from [Content] onto the relevant day in the calendar. Then you don't need to have separate formulas to return the 6th smallest, 7th smallest, and 8th smallest row indexes. A single spilling array formula in each day mini-block handles that automatically.
I've made the structural changes to the [Calendar] sheet and replaced all of the daily formulas with the one described above. About that formula...if it ever needs to be modified, it would be entered in the upper left of the calendar and pasted into every other column directly below the day number. After this is done for one week (the top row of the calendar), that entire calendar row from A:N is copied and pasted directly under the day numbers for each of the other weeks in the calendar block...and you're done. Here is a link to the revised template that will accommodate 8 rows (10 during one week):
If you have more than 8 items to display on a day, select the top row of the calendar just below the day numbers (not the entire row of the worksheet, only the calendar portion), and insert cells with the "move remaining cells down" option. Insert enough rows to accommodate all of the content. This moves the spilling array formula down, but it avoids an error message that will occur if you try to insert a row within the spilling array range. Next, copy the formula that was moved down by the row insertion--and here I mean copy the formula WITHOUT the leading = sign. Do this for the first day of that week. Then go to the newly inserted row below the 1st day number for that week, enter an = sign and then paste the remainder of the formula. That should preserve the references so that no further editing of the formula is necessary. Delete any existing formula in that day mini-block and if any content matches that day, it should automatically spill. Then delete the remaining formulas in that week. Copy the formula you most recently re-installed (for the the 1st day of that week) and paste the formula under each day number (6 times).
I'm not entirely clear about your description where you mentioned adding "2 more statuses". The [Content] sheet has 6 "status options" as well as a scheduling table with a "Status" column heading...cells in that column use data validation dropdown lists that refer to the "status options". Are you saying you've increased the number of status options from 6 to 8?...or have you added some items to the scheduling table and associated each of them with one of the existing 6 status options?