Able to command a higher monthly rent from both units Lessons learned?

Current value is approximately $220-250M If I sell or would command rent of $1,600 a month vs $900 mortgage if I don’t.

Then do a deep dive on those properties to explore those specific areas and the rents those assets command.  

Just like in a SFR, a nicer place will (should) command higher rent.

Overall they're sound for the crime rate metric and are commanding strong rents because of its access to the city and local amenities. 

I am around crews of guys in their 50's ( including myself ) At this age and level of experience we command top $$$  and we get it . 

How much to expect,  as you said, is totally up to you and how you value your time and the opportunity. i would put more value a  note that is in  Texas, than  a note that's in Detroit, Also, look at risk. you should command a higher yield on a re-performing second. or a higher yield on a note that's located on a judicial state.  

I really want to handwrite letters to these potential motivated sellers because I have to believe that handwritten letters would command a better response rate.

@Jared Vincent - Generally an entire command gets moved or deployed at the same time, but not always. 

Not only would it attract the best tenants, you can command the highest rent, and it is a renovation that will sustain over time.The question of 'over-renovating' is always in question but ultimately this is a property that you're going to have for a long time, you will make it back in rents and appreciation for the home to come.