If something comes up very appealing then maybe sooner than later.

Units are rented (and sold) on appearances of kitchens, baths and curb appeal. 

Some companies offer different plan options that can be appealing based on what services you really need. 

I'd like to look into multi-family properties as they seem most appealing to me, but I've also done some research into more hands-off models like syndicate groups or crowdfunding - does anyone have experience with these in Ontario?

It also appealed to me that I could help someone stay in their home (my primary exit strategy) and still make money.

Next to curb appeal, the first things people notice when they walk inside are the ones that affect their senses, like sight, sound and smell.

I definitely see the appeal to owning a property outright though

Being able to collect a commission on a buy is nice and waiving or reducing your commission in exchange for a price reduction can make your offer more appealing as well.As an agent buying properties, you will be held to a higher standard and must adhere to your states guidelines when dealing with sellers.

Either of those seem appealing?

If the property is in an area that you believe will appreciate one day (arts district, natural appeal, etc) and will also produce positive cash flow, then I don't think anyone should fault you for taking that deal.