However, I'm running into some issues based on affordability.

The inspections can be pretty frustrating, but guaranteed rent for that asset class is valuable.

Parking is tough in New Brunswick, and this may be a good more affordable alternative.

If you earn $50-$100k with the ability to select the neighborhood you live in, you probably are looking for a safe, well maintained, nice looking, updated, affordable home, in a neighborhood of similar properties, in a good school district, with easy access to shopping and parks and your work.   

You'll find more affordable prices and it'll be easier to house hack. 

I can afford the single family much quicker, but don't want to delay growing my portfolio (granted I still would with a 3rd SFR) just to move into a larger house i don't necessarily need right now.

On the investment side finding anything with an upside is becoming increasingly difficult and finding affordable housing that is not a trailer is near impossible.

So if a property doubles in value you property tax will only go up by the capped maximum (I think 3% but it may be 2% - I used to know but do not really care about the 1% difference now).So at your income you will be challenged to find a place that you can afford with a safe reserve. 

What is the biggest frustration in your business?

By no means do these updates have to break the bank, but they could could help to ease potential frustration.