Hostaway is a short term rental software but with enough finagling you can get it to work for mid-term as well.

Curious if anyone has had any luck managing all these aspects in one singular software?

It should be handled by your tax software or, better yet, by an accountant.You also have an option of paying the entire capital gain upfront, which is usually not to your advantage, however in some situations it could be.

It doesn’t take long with tax software but if you can save current tax dollars today, many think its worth it (not considering the strategies to avoid recapture as well).

I have demo'd and used various Property Management software over the years. 

The software system I was using for payments notified me that he paid rent, but it did not proactively notify me that one of his payments bounced back.

The built in marketing campaigns intrigued me the most as I wouldn't need to pay for a 3rd party software/system  and zapier with Rei Sift and being that I currently only use SMS, email and cold calling, Invelo would allow me to add mailing and RVM to my arsenal . 

FSBO's almost always think their property is worth more than it is, are difficult to schedule showings with, haven't prepared the property to sell, are unwilling to negotiate, and they almost never know the sales process or have the software or the contracts to make the transaction go smoothly and keep the deal from falling apart over little things (very common when there are no agents to act as mediators, buyers and sellers have inherently opposing interests and tend to argue then cancel the deal).

The stuff they do is easy to automate with software.

Do any of you have virtual numbers or do you find that your PMS software or messaging through Airbnb and other booking platforms are able to fulfill you communication needs while keeping your personal cell information private?