It simply depends on your time frame, when you want to actually begin renting the property out short term, and what the loan terms are.

Cleveland, Ohio is a great market to focus on for cash flow and specific pockets have gone up 2x and upwards of 4x in the last 5-10 years even!

Merry Christmas and Happy Holidays!

You don't say where you are located so I say start close to home and work from there. 

If you want flexibility and liquidity, Option 2 might edge out.

Work currently in the accounting field and I’m a licensed CPA in the state of Ohio and West Virginia. 

.+1 to @John Underwood and @Andrew Steffens

@Dan Groveyes, go to meetups (real estate or business) and meet people in person and build a networkbut... no offense... i don't think funding an entry fee in second position is a particularly compelling investment

Now I'm on the Panda Planner and actually like it better. 

Realtors have likely walked through and done a broker walk through.