Look at some YouTube videos by Anderson Business Advisors.I am not an attorney, CPA, only a long-time investor. 

If you have not been to Milwaukee, YouTube is a good start.

You have gotten some great advice already in here but I will touch on the guest experience portion and local partnerships.My tips for guest experience:Have a digital guidebook explaining everything inside and near by places to visit.Record a YouTube video of yourself touring the property and showing the details of working things.

I’m a big fan of a YouTuber Attorney named Mark Kohler.  

I have found that AirDNA provides data that can be somewhat accurate to highly inaccurate.It is just an algorithm.

This is my slow part of the year, and I do all the things to move the algorithm…fiddle with order of photos, change seasonality in my photos, tick as many boxes as I can, fiddle with pricing.  

Starting smaller is fine, but the unit has to be spa like or you will likely fall victim to pricing wars or get lost in the booking sites algorithms. 

I would recommend checking out his YouTube channel and his website: "robbeardsley.me" . 

I did a very similar automation campaign for my guests.One useful tip  (you covered it on finding the apartment) is that I like to record a full walk through YouTube to show how to work things.

In my opinion, anything that's not QuickBooks or Xero is just a watered down accounting software.I made a video about this on my YouTube channel, BP isn't letting me share it but PM me and I can send you the link