I would then probably consider putting down the min. downpayment on a duplex up to a fourplex, for a place to live and rent out the remainder to  cover the mortgage and expenses.  

Perhaps 5 years into the future, when I have a more stable life and future plan, I can use that cash flow that has been accumulating over the past few years to fund a flip and potentially make some serious money.

I put my criteria clearly in the listing: 3x income over rent, 85% on-time payment history on credit report, and good references from past landlord.The biggest mistake you can make is taking the word of a current landlord.

Since I have done both of these things wrong and right in my past, I can tell you keeping the client happy to a certain extent is a lot more cheaperWe have found that setting the proper expectations right up front of what we will and will not do seems to help solve going down this never ending rabbit trail sometimes.

I didn't need to use them much, but I used them for three flips in the past I think so it could work for your client.

I've been house hacking and renting another room in home via Furnished Finder for Midterm rentals for the past year.

While this hasn't been needed in the past, I’m considering if it could help prevent tenants from reporting problems later that they claim existed when they moved in.

Here are my initial thoughts:As a small landlord in Ontario, my experience over the past eight years has highlighted significant challenges in managing rental properties effectively.

More likely now if you find a willing property owner you will sign at best a 24 month lease lets say at $3,500 a month for a nice 3/2 with a pool 5-10 mins off beach. 

Here's some other copy & paste advice you might find useful:---------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?