One of their friends is managing it until they can find someone more permanent.

I’d like to turn my home into a permanent rental and buy my next investment property.

Property Transfer Tax - We have transfer taxes when you buy a property based on the fair market value of your home (based on the following scale):  1% on the first $200,000,2% on the portion of the fair market value greater than $200,000 and up to and including $2,000,000,3% on the portion of the fair market value greater than $2,000,000, andIf the property is residential, a further 2% on the portion of the fair market value greater than $3,000,000 (effective February 21, 2018).Additional Property Transfer Tax on Foreign NationalsAdditionally if you are a foreign national: another 15% tax of the fair market value of your homeSpeculation and Vacancy Tax - if you own a home that is not your primary residence and is not rented out for at least 6 months of the year you pay an extra tax 2 per cent for foreign nationals and satellite families who do not pay income tax in Canada;1% on the first $200,000,2% on the portion of the fair market value greater than $200,000 and up to and including $2,000,000,3% on the portion of the fair market value greater than $2,000,000, andIf the property is residential, a further 2% on the portion of the fair market value greater than $3,000,000 (effective February 21, 2018).1 per cent for Canadian citizens and permanent residents who are not resident in B.C. for income tax purposes (and not members of a satellite family); and 0.5 per cent for British Columbia residents who are Canadian citizens or permanent residents (and not members of a satellite family).

I wish I had a solution to offer those people, but with the affordable housing shortage already being a severe crisis in much of the area, now aggravated by these disasters, many people are having to say goodbye permanently.

Your end plan needs to be to get rid of this tenant permanently asap before she causes a infestation in the entire building. 

It's been driving me nuts that for every little job that I'm too lazy or incompetent to do I have to pay someone else hundreds of dollars just to show up and take care of it, but I don't really have enough work to hire a permanent worker (16 units in Austin).

Best thing is that these funds roll into permanent financing and you don’t have to wait years to save enough money or get motivated to actually redo that kitchen.

If you are planning on holding more than a couple years, I would have a plan for permanent financing on these properties.Finally a question, when you boss says go Multi Family, are you sure he means a triplex?   

I feel like I could be pretty resilient from investing in the stock market for a few years but I guess I will never know if a bad deal would permanently scare me off or not since I've never owned a home before.Do you think rather than finding an amazing deal it would suffice for now simply to find something that could reduce what I would be spending on rent somewhere and then continue to search for good deals?

On the off chance you decide to hold and rent, make sure you discuss permanent financing options with a couple of banks/mortgage brokers up front as well.