It sounds like you want to get into rental property investing so you want to make sure that you are with a company that has an investing mindset and can create an environment where you feel comfortable and motivated.

Also not sure if you own a house but you could leverage that if you feel comfortable with it. 

When you are house hacking with kids, you have to place your family's comfort level first and the investment second.

However, I wasn’t comfortable taking the risk of waiving the inspection contingency and out of the 12 offers, we lost.

Getting the property inspected should give you a decent amount of comfort, but I would also follow up with inspections from contractors for anything that even seems close.

And what you are comfortable paying per month divided that by the hours and day Maybe like 25 a week that 100 a month if u have 4 times a week garbage. 

Strategy BRRRR sounds appealing, but certain aspects seem too similar to house flipping, which I'm not comfortable doing.

Does anyone have any tips on how to get around this problem to make people feel more comfortable with this option period?

However, if it's a comfortable driving distance from Toronto (or some other populated city) I would definitely look into Tiny home/Cabin rentals as they are low cost to build and can produce a great ROI.

One of my clients had his wife lose their job a few days before closing and although they could get a loan and close on the investment/rental property, they did not feel comfortable moving forward with the uncertainty.