My advice on the tech stack is to make sure you consider your long term goals and make sure that what you buy today integrates with tools on your wishlist for later. 

I used hospitable for some time and I liked it but I needed a PMS that could integrate with my locks, I use erentalocks because when I started my journey with STRs (I have 4) I was not sure about the internet in the area. 

Not being an attorney, I cannot judge whether such structures provide the legal benefits they are meant to provide and whether they are necessary.My main beef (substitute soy if you're vegetarian) with them is that investors do not follow the burdensome formalities required to maintain integrity of these structures.

Podio integrates with so many 3rd party tools that you can pretty much do anything you want.A few other things that I have setup are...Automatically pull property information and comps from Zillow into PodioGet Google Maps Satellite and Streetview images for every leadCreate documents on the flyManage my direct mail marketingLead Tracking from initial lead to Deal or DeadTeam Meetings with GoToMeeting Freeand more...The only limit really is having the time to think of what to do and how to do it.