I stay in Canada but have several USD in my Canadian bank accounts. I'm not good at finance, but since 1 USD = 1.38 CAD right now, is it wise to convert some/most of my USD to CAD right now assuming it won't go above 1.38 in future? Or should I keep it in USD which is the stronger currency?

I wouldn't keep any USD unless you have a specific need.

I would keep some USD. You will travel to the states and it sucks having to convert, especially when you need to pay a premium.

But if you live in Canada, the majority of your holdings should be CAD

No. I would keep as much in USD as possible.

The fundamental picture for Canada has not changed, and their budget will continue to be challenged by low energy prices while non-oil sectors of the Canadian economy continue to underwhelm. Even a 25% rally in crude from these levels would likely not create or save any jobs in Canada. The Bank of Canada no matter how optimistic they sound will likely cutting rates again later this year. The Dollar has not turned.

Think of the trend of USD as smile-shaped. On the right side of the smile the US powers through the current global economic turmoil, the Fed keeps hikes rates a few more times, and USD continues its uptrend (also downtward pressure on oil). The left side of the smile is hard-landing everywhere, fear-mode, repatriation and USD will appreciate.

Either the US economy shrugs off recent weakness and remains the shining light in the global economy, or the rest of the world drags the US into recession, denying itself the consumer of last resort. In either scenario, repatriation continues.

Right now expectations of a 'mild' US recession and some poor data is the only thing keeping USD in the gutter of the smile. USD/CAD will be back re-testing 1.47 before the end of the year, if not the next 3-4 months.

Keeping cash accounts in a foreign currency is only slightly less dumb than buying physical currency to capitalize on a long term forex movement.

I'm actually confused. These USD are from online poker winnings back in the day. So I have a choice to keep them in USD in my bank account, or convert to CAD. Looks like there are varying opinions on whether I should convert or not?

What's the reason? These are funds I'm not going to use right now.

So are you saying I should convert then? Or should I NEVER convert unless I am going to need to use them?

Well, your question was:

"is it wise to convert some/most of my USD to CAD right now assuming it won't go above 1.38 in future? Or should I keep it in USD which is the stronger currency?"

My answer is:
1) no it is not wise.
2) It WILL be going above 1.38 in the future (likely this year and a lot higher).

You should determine your own risk tolerance and time horizon regarding "when". I'm not exactly sure what "several USD" means in your bank accounts, but if you will need lots of CAD "in 3 or 6 months" for a personal purchase or otherwise, I would hold onto the USD until then. Wouldn't be upset if I was forced to convert at 1.47.

Kevin O'Leary (a Canadian) is very smart with some very good advice on this exact topic. Just start watching some YouTube videos.

For me the answer is keep like 3-6 months of expenses in the bank denominated in what ever currency your expenses are in.

You can then look for the "cleanest dirty shirt" if you want. But if you want to keep more assets than the above in cash / a cash equivalent gold (and maybe BTC) are better than any of the currencies long term.

Your post is asking if what we think that future holds for usd/cad exchange. No one knows.

If you're going to keep usd, then it should be because you think it will be worth more relative to cad in the future.

If we knew the answer to this we'd all be forex trading and making millions.

You live in Canada. You minimize risk by having the majority of your holdings in the national currency.

I think it's fine to keep some in usd as a hedge and for travel. This isn't a question any of us can answer for you. Do what you feel is best.

And this...if you're going to hold usd for no particular purpose why not hold gold, or apple or Facebook or Yahoo? Personally if i was you I'd get btc and eth

Yeah you're far better holding a dividend paying, good value US stock than USD (or CAD) if you're barely using the money.

^ Holding USD securities while being in Canada? Wouldn't there be issues?

Also, any suggestions as to what's the best investment? Mutual bonds? Stocks? Any specific ones?

Get some gold and some bitcoin.

Make an account on www.kraken.com for bitcoin. It's easy as a Canadian.

Gold: Very high transactions costs, zero return
Bitcoin: Ultra high risk, even old hands are selling out here.

TS is a skeptic when it comes to these two. But he does have valid points.

Of course it is easier to own domestic equities than international ones. But you would hardly be the first Canadian to own US equities. I am sure you can do it if you set your mind to it.

Also, I am sure there are some good Canadian companies. In fact, on this very subject...

1. Sprott is Canadian look into some of his offerings if you are interested in gold.

2. Canada has lost of good companies in the mining sector. I'd look for producers with little to no debt that pay dividends.

^ So you suggest buying equity instead of gold? And are either of them tax-liable?

IMO they both have their place. Gold (physical in your hand) has no counter party risk but also doesn't have any cash flow.

Equities can / should have cash flow.

Get a financial adviser

Dont pay anyone for this.

^, ^^

Ha, I almost posted saying 99% of them are just straight trash. Believe me, they are. It is a networking game for them, not a risk game...

But which is a better investment in the long term??

Equities have excellent returns long term, gold returns ~0% long term.

Someone recommend this guy a good book on investing basics.

How much value does this post provide the OP?

If he wants to capitalize on macro forex trades he shouldn't even worry about moving money in bank accounts.