She has also presented me deals locally and OOS.Realtor: Through Redfin/ zillow / har - spoke to a couple of realtors then picked the one I liked the most.Property mgmt: google search / BP- interviewed at least 3, picked the one I liked the most.

Would you rely on your realtor to pick this up for you during due diligence? 

I would recommend picking up a copy of the BiggerPockets book, "The Book on Estimating Rehab Costs."

Pick up 2 extra jobs, move to a cheaper (or free) housing situation and live like a pauper (this is temporary sacrifice for Massive long term gains). 

That said I do mostly wholesale and just pick up the occasional rental.

I am purposefully picking rehab items that would likely improve the value by an amount above their cost.

OR say you do send a letter and/or picture that might also make the seller not pick your offer.

I would say something to the tenant (text or e-mail-wise) similar to: Please let me know when you would like for me to pick up the signed lease.

In 2024 you can pick which has the better market value and potential and rent it that way. 

A great place to start is to pick up "The House Hacking Strategy" by Craig Curelop to learn more about the process.