Thus, focusing entirely on residential throughout your life by necessity means that you will reach a scale barrier that will be difficult to jump past without additional effort and risk exposure.

As he becomes more experienced, like yourself, he can then judge the necessity for a title search.

For an estimate of this size, you absolutely need a second opinion on the necessity of the repairs and you also need comparison pricing. 

STRs are not a necessity but rather a luxury.

Why do you feel the necessity to get your license in order to invest?

My suggestion is to make sure it's a house that other students will be in line waiting to help you keep it rented when/if you move on to another area, or town, and one that is very close to campus (walking distance is often optimal, but not an absolute necessity) might be helpful, but I believe making it an attractive-to-students house is important.... 

They have to out of necessity.

It's a luxury, not a necessity.

Multi-Family is a necessity.

The owner most likely is in an exclusive contract with the agent so including them will be a necessity, but in my opinion you can make a deal with the owner you just have make sure that you factor in comission for the brokerage.