There are classes of income/dividend producing securities (i.e. 10%+ yields) that are doing really well, so extremely passive and extremely liquid. 

Payroll paid weekly, utilities monthly, meat/produce 3 day. 

There are some missing pieces of data needed to make an in depth analysis from where we sit and give you more sound advice, however I own/manage property in Tampa which is a highly producing market and:- With $300k to play with you can acquire a $1M property or more which does provide the best cash flow- On a $1M acquisition and $200k (or less down possible) you can achieve 10-30% CoC returns, likely 15% inclusive of management is possible.- Do not forget about appreciation, which is where the real wealth comes from. 

Is the cost to produce a median home any less?

I know people are comfortable with losing money in the short term until rents and appreciation catch up, but as this is my first property, I don't necessarily want to buy something that produces neg cash flow.

Some offices have fees and others may pay expenses to cover you and expect you to produce.

You would almost be better off going into the lending industry and leveraging your resources to produce interest income.Purely my opinion ...

It's currently rented out but isn't producing any positive cash flow, I am breaking even with it.

Just don't get caught by the slight inflation this summer's lack of inventory has produced...  

They could list it on the MLS but that usually produces low offers.