What steps do I need to take to make sure I can get this going as smoothly as possible especially when it comes to resale in the future?

It presented itself at a great price while I was on the hunt.

It does not matter what the seller wants.

We feared it was too low, but we were not willing to accept anything more and left it in Gods hands.

Took an extra 6 weeks than planned,  but ultimately got it done. 

Some of course may walk and not do anything to protect their homes.

Based on numbers may not work as a DSCR anyways but what was the contributing factor for bringing $ to the table - then others can address it more clearly and see if its an expensive DSCR loan or somehing behind it.

Lots has changed over the years.Managing it yourself from a distance can be done, but it will require your team to be built and for you to have back up strategies if guests need attention and you're unavailable. 

Do you handle this through the platform (AirBNB or VRBO) or outside?

In my opinion, it's at the far end of the un-sexy-but-profitable scale.