I have 5 different T5008 info slips and one Outlays and Expenses amount. Do I divide this one figure into 5 to enter on my tax return or as a singular amount on just one return entry in turbotax.

Further to the expenses reported from my Brokerage Firm with a T5008. Do I simply declare all expenses against the capital gains reported on the T5008?

why are the questions being asked not being answered by Turbotax?

Well, the original question of "What is an expense or outlay in T5008?" was answered back in 2019.

If you are asking about how to report your outlays & expenses, if you don't want or can't enter them on your T5008, then you can enter your expenses in the Investment Expenses section. Use the “Find” tool 🔍 to search for “invest”. Select “Investment Expenses” from the list and then click the “Go” button.