@Ryan Burke why is this a concern for you? 

I HAVE read in certain tax guidelines about how passive losses that pertain specifically to depreciation cannot be used to offset capital gains from a different passive investment...but it still wasn't perfectly clear. 

My biggest concern at the moment is estimating the rehab costs. 

It sounds to me like the seller doesn't want you in the property and that would concern me.

Should that be a concern or should it allay concerns? 

As a former student myself, I’d prefer to live on the West side as well.My only concern about the West side is I feel that the student rental market is over saturated and would be worried about finding student renters each year.

My biggest concern is figuring out the most I can pay for PITI and still come out on top renting it out.

I have considered creating an LLC and deeding properties into it but am concerned about "due on sale" clause.

That is my first concern, I do not see a fair way it would be symbiotic for the both of you.

I'm using dealmachine for the lists for a direct mail campaign.my concern is the houses that are owned by a corporation or out of towner that is most likely STR the home.My question is how do I get my letter into the owners hands.