Trump as president and US stocks in TFSA and LIF

Making investing decisions based on situations like this is very difficult and does require a degree of speculation.

Ultimately, hedging is up to the individual investor and their particular tolerance for risk. Generally, the guidance is the lesser your time horizon, the more incentive to hedge. For someone who has 10,15,20 years left in the markets, because currency fluctuations tend to even out, hedging doesn't really do all that much besides cost you fees.

However, for someone who is in retirement or nearing retirement, hedging can provide a bit of a buffer because like you said, a material swing in the price of the dollar could impact the cash flows you rely on in retirement.

The one thing I would maybe say is would a swing in the CAD relative to the USD really "evaporate" your gains? How long have you held the positions for?

There are too many individualized situations for me to ever provide any sort of concrete guidance in regards to something like this, as it is so investor specific. A prime example of this would be someone who is a snowbird and lives down in the US for extended periods of time. In that case, it may not be wise to sell of the US holdings because they can utilize the USD dividends generated to spend money while they're down there. This is just a simple example of many, many complex issues that arise from a situation like this, but just kind of stating it so I can highlight how it's impossible for me to provide individual pointers.