Ask yourself: do I really have the knowledge of real estate principles, real estate law and real estate finance; the network of contacts; the experience both in business in general and real estate in particular; the time available; and the analytical ability to compete against FULL TIME EXPERIENCED PROFESSIONALS to be successful in a field where the failure rate is so astronomically high?  

Real Estate is a belly to belly business.

I know you can do one per but that would be a hassle if you scaled your business.

If so they may have a real estate license or they may work with an agent that relies on repeat business rather than a one-off purchase. 

I average about $2000 a month in cashflow on the current rental property, and the new property would bring in around $3500 in gross revenue.

You can find qualified buyers that are small business owners, tradesmen, etc just have someone qualified to do prop underwriting be fore you sign the agreement. 

With a push to bring more manufacturing back to the U.S. and more employees returning to office work, there will be a greater need for mass transit solutions rather than building more roads lowering the quality of living if you want that SFH with a yard.

I would be leveraging my relationship with my family member to wholesale the property for experience and getting them for investment in my real estate business while my family member gets rid of a property, hassle free, while getting paid.

The new people don't know and they are the business target.

It lists for an average $250/night which brings in $7500/month.