Likely, but you're ensuring a (potentially) happier and more loyal tenant for the long-term. 

What are the potential pitfalls or challenges in launching and running a title company?

Not only are they knowledgeable but they can potentially get your plans through quicker. 

I started marketing on multifamily trying to find potential good sellers.

Specifically, I’m drawn to distressed properties, such as pre-foreclosures and foreclosures, because of their potential for strong returns and lower acquisition costs which I feel is a great combination for a new investor with my budget.That said, entering the U.S. market as a Canadian comes with its own set of challenges, and I want to make sure I’m approaching this the right way.

I'd like some input on wrapping my head around a potential first house and if this sort of deal/rent makes sense.

You'll have quality tenants, minimal hands-on management, and lower potential maintenance issues.

Because, think about it, if you are new what value are you bringing to the equation other than potentially money?

Validate zoning, potential special or use variance, future zoning map, neighboring zoning.

However, I have no idea how to choose from the remaining cities, it seems there are a lot of potential options:- Midwest - Michigan (ie: Grand Rapids) seems to have options, also seeing Columbus Ohio and Indianapolis coming up- Reno - I've seen mentioned several times on here- Pittsburgh / Philadelphia / Twin Cities - All mentioned as lower cost to get started, and seem to be experiencing growthI'd ideally like to find a place that has strong potential for future growth, a diversified economy, and I don't mind living in (being close to nature would be a plus).