Ideally it would be beneficial if this is also in an area that you would have interest in visiting from time to time since it is a good idea to still check on properties in person from time to time.

The ideal strategy for you depends a lot on your network and skill set.

They only deal with title & "paperwork"   which with my experience I deal with that, while the buyers make sure what they are trying to do is possible.

(condos are cheaper, but not always ideal and the condo fees take a lot of the rent that could go to your mortgage). 

Given the abatement option could you continue to occupy 15% of the building with commercial tenants while the rest of the building is converted or is that a logistical nightmare/ideally are you seeking different long term commercial tenants if you go that route? 

Ideally, the software can integrate with my google calendar. 

You need to showcase the 3 pillars of conversions, in a light that aligns with what that audience's ideal cash buyer to work with is.Social media is a perfect outlet to showcase who you are, what you are like, and what it would be like to work with you, all of which are essential requirements for a conversion to take place.So Social media is not just another strategy to try out on its own stand-alone.

I have just over $200K left of owner-financing, but I'd like to obtain a cash-out mortgage/loan of $500K (ideally) to be able to pay off the previous owner and make some repairs, etc. 

Having two people paying rent, but only one living in the house is not ideal unless both understand clearly they are liable. 

I had large payments on my personal loans due and extra money going out to finish the project, not ideal.