I understand real-estate is cyclical, and some times may be better than others, but regardless, it trends upwards over time.

@Yamin Htet just make sure you don’t leave the building if you’re looking to rent less than 28 days.

Is it worth hiring someone to take care of the appeal rather than doing it myself? 

You're in the perfect place to learn about real estate investing.

When it comes to the actual purchase, you might be able to {gradually} purchase shares of the business (depending on how it is set up and the appetite of the owners) rather than an all out purchase.  

The duplex is currently in my name but was paid for in cash by a family member's line of credit.

Owners come primarily in two flavors...the Micromanagers, that know more than you; and those that prefer being oblivious and not bothered with anything but the most significant incidents.What I have focused on is developing solid systems and processes in all operations with the goal of prevention, rather than constant corrections.

Less concessions in a weak market = more vacancy.  

So I really don't have details on it, other than when I saw the posts that there was not one person that said it showed a great increase in ADR.

He than stopped the transfer because he did not like the terms of his mortgage.