Does anyone who's taken this approach have any advice or tips?

I have been wondering what will be the better approach between: 1.

Approach the owner.

That requires way more experience and designations. 

Or brand new with a more hands off approach with the hope for more appreciation?

The real estate professional designation has nothing to do with 1099 reporting. 

No dwelling designed for occupancy by a single family shall be occupied by more than one family, nor shall any such dwelling exceed two and one-half (2-1/2) stories in height.

@Devon Martin Hey Devon, another approach is to buy something that is relatively stable, meaning that it has tenants and maybe ONE vacant unit for you to move into. 

There was a condo in Scituate harbor that had been on the market 856 days at another agency.With 30% commercial, I knew it wouldn't go FHA/VA/Conventional, so I approached a community bank down the street and got them to proactively look at the property and agree to a portfolio loan.I'd recommend that same approach. 

Is it the interpretation of the law as brokering a deal ( which I agree should only be done by a legal and licensed entity and understandably varies by location), is it the approach that wholesalers may take interpreted as predatory or is it something else?