But if you have to jump through hoops or spend a significant amount of money to put it in might not be worth it. 

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

I'm completely lost at why people would spend money on class and workshop, when they can actually use that money and go find deals a bit outside of the expensive city we're in. $8,000 could got you started on a deal, or do a mailing list of some kind.

Unfortunately, this costs $$$ that you shouldn't have to spend.

Also control the thermostats so the tenants don't jack up the heat in the winter giving you a massive bill.

Don't spend time looking for something that doesn't exist.

I'm going off the understanding that you still need to spend 500+ hours in the business to achieve material participation (please correct me if I'm wrong). 

If there was no appreciation, there is no need to do a 1031 exchange.I have never been a fan of condo's as you lose some control over the investment - You have no control over the monthly maintenance fees, you may not have control over who is on the board, you have no control over special assessments.I wish the investments turn out well for you!

@Ed Lopez what controls do you have over what they decide to do?

i think you can be successful if you are willing to do what you alluded to, which is spend time in person in your chosen market.