Would two hours be a decent amount of time to connect?
I suppose there could be delays which cause us to miss even the second flight which is five hours difference.
There is no guarantee for either - therefore travel insurance is needed - does travel insurance cover a missed flight due to delays?
I would not do a two hour connection on separate tickets. Five hours is a maybe but I'd be more comfortable with much more. "do you feel lucky"
I suspect travel insurance will look to the airline responsible for the delays to pay for the costs incurred due to the delay (if weather, then insurance should pay, but if a mechanical, then the airline should pay and look after you, but if on separate tickets, then the airline will say "insurance"). Separate tickets, then "self insurance".