I'll be doing an extensive full gut remodel which will include an expansion of living space by doing a partial garage conversion making this 2 bed 2 bath SFH a 3 bed 3 bath SFH, adding about 300sq feet of living space.

Some options I've considered are finding houses with convertible space to add square footage but I worry that the cities will just not permit those conversions.

For some reason the later fact always gets left out of these conversations...

I would love to have a conversation with you. 

My point is that a face-to-face conversation can go far.

But some of the conversation I had with this dude is what stuck in my mind..

It might even be worth it to reach out to your contractor for a quick conversation. 

You will know from your conversations who is a right fit for you and who is not. 

After several conversations with OOS investors and many affiliated brokerages it still amazes me that the secret is not out...

The structure has to either already exist (we converted the garage) or you can do an addition to the property and build it out that way.One of my clients took an illegal garage conversion that was expanded into two bedrooms and used the FHA 203(k) loan to get it permitted.