My original plan was to utilize a real estate agent to be my property manager that I met through a Dave Ramsey referral program, but I'm exploring if I should attempt this on my own.  

I remember when they put this is place in Portland, OR and there was a ton of interest.  

My preferred options are:1. house-hack with a duplex under ARV; live in one unit => renovate => rent the other unit2. buy a SFH under ARV that could be converted into a duplex (preferably adjacent units vs top/bottom) - I'm assuming the biggest challenge with this strategy would be separating the infrastructure for utilities; and costly.

Was at one last week that included City of Calgary who did a presentation on legalizing illegal suites and accessory suites in general

I would think there would be a ton of pressure from them.  

The plan was to utilize the HELOC as the down payment then getting a conventional loan to cover the remaining 80%.

As an owner of several short-term rental properties, when my guests have an issue at one of my properties, I do everything I can to make it right.

The benefit to these is you get your foot into the door without a ton of capital and as time goes you can move out and cashflow on the property.

I haven't seen anyone utilize an elevation cert to reduce the flood ins premium but it wouldn't hurt to reach out to insurance agents and see if it's possible. 

When I was pursuing that at one point I only had 1 out of 50 applications reach back out.