I guess my big question is do I need to choose a title company and schedule the closing or how does that work? 

My guess is that he doesn't have a bunch of these to choose from.Honestly if he must have this place and only has 5% move in for a year.

Plus, the bad reputation keeps less savvy folks out of market which is good for them and for the city/area.

Will be finished with undergrad in less than 2 weeks with a BBA in finance.The title of the post is misleading because I'm not choosing either or.

Additionally, to increase my deal flow, I will use local reputable property managers to manage the day-to-day activities of my rental properties."

Choosing the right hosting, designer, seo partner and marketer is what will separate you from the rest of the pack. 

It is hard to make the numbers work locally for cash flow residential, but I'm a DMV native and so I choose to invest locally, where I understand the neighborhood and growth dynamics,  and where I can manage landlord issues locally. 

Most reputable lenders are going to want you to have some skin in the game.

I think you would still get some valuable experience by running this deal through a reputable hard money lender and seeing if they would fund it.

Overall there is nothing stopping an agent from doing this, but reputation is a huge part of the business so it wouldn't go well for most.