You should really do the research to understand your market before you can trust a software to appropriately set rates for you.  

I am currently researching the different regulations in Ontario and GTA.

I will continue to research the topic as you suggested and hopefully continue to learn more about it.

. - Before choosing a password manager, you should do some research on it.

The Raymond St deal came through local market research and networking.

The only way to answer that in general (whether house hacking in today's market is still a good option) or for a particular property, is to learn how to run the numbers and analyze a specific property to see whether it will be able to stand on its own as an investment when you move out someday.There are a lot of resources here on BP for doing that but I'd just say, make sure the assumptions you're putting into your spreadsheet or deal analyzer are realistic.Make sure the rents (especially for vacant units or pro-forma #s) are realistic by doing your own rent comps; make sure the mortgage rate is realistic by doing some research online and/or talking to some mortgage folks; make sure insurance #s are realistic by getting a couple of quotes for the # of units and zip code / area you're looking in; etc.I hope that helps, and good luck 😊

There could be opportunity for urban in-fill with tiny homes, and I know several folks researching that possibility.

It's a question that is impossible to answer without some market research.

Unfortunately, researching websites doesn't give me clear, straightforward answers that, yes, they have expertise in this particular real estate strategy.I'm specifically looking for attorneys in RI, MA and FL.

Things like landscaping/snow removal and labor cost for repairs are going to be highly variable based on your market so you'd need to do your own research on the going rate by either talking to other local investors, running your own google search, or exploring basic services on thumbtack/angies list etc.