My hope is I can gain their trust as a property manager and eventually be the one they turn to to sell later on or refer for business in the future.

Consider the "2 of the last 5 year rule" to avoid capital gains. 

Companies typically last only ten years on average.

Typically they will have referrals to local accountants you can interview. 

After five years you'll have earned $90,000 in rent income and gained $34,000 in appreciation.Buy four houses with $50,000 down on each.

That being said real estate investing is typically a long game and with just 2 years under your belt you’ve just started.

Some carriers don't ask but you should make sure that you're not indicating (in the policy application that is typically e-signed) that you aren't using your property for student housing if you are.  

The people doing subject-to are quite sophisticated and typically have quite the platform.

. - Just be prepared, because a motivated seller typically has a property with issues you need to be sure you can solve.

The cons as i see it include loosing the 2 of 5 year cap gain exception, typically not an ideal rental because the emphasis at purchase was buying a good home for your family and not a rental with optimal return (my ex-home consistently has the lowest cash flow for equity in my RE portfolio), not disconnected enough from the property causes addition angst on damage and may result in over improvement.