She or he is themselves an entrepreneur, perhaps their exit plan is to get the business up and running, and then sell it somewhere in that 5-10 year window. 

I am planning on mainly looking for properties in Maryland and in Florida.Excited to be here!

I hope to start him similar to your plan but quickly transition him to sophisticated value adds. 

Drive around the property and its surrounding area to get a comprehensive understanding of the location.

Want to impress clients/banks/investors then put together a great business plan and come in with some numbers that work.  

I'm currently living in one side of the duplex and planning to rent out the other side.

Or in other words, if I intend to live in the property.I plan to buy a multi-family property.

Search for properties in line with your spending plan and investment objectives.Property analysis: Examine possible single- or multifamily properties to ascertain their overall investment viability as well as their cash flow potential, cap rate, and return on investment (ROI).

If I can score some cash flow, I'll take the win, but my plan is to at least break even in payments.

We plan to use the home currently for about maybe 2 months out the year and would like to rent it out the remainder of the year on Short term rental.