Only thing worse than not raising capital is raising it and then having the market work against you while you operate to the best of your ability and still get crushed by that which is outside of your control.I just watched a multi-decade veteran likely lose 100% of my investment, after executing his plan to the best of his considerable abilities.

Economy of scale would help the overall monthly cash flow on a multi.

Are there any ways i can qualify for a loan on an investment property that produces cash flow ? 

Are there any specific considerations related to barns, pastures, or riding arenas that we should keep in mind?

What I would encourage you to do is to compare how much cash you currently have invested out of pocket in the deal and also calculate what the cash flow is for that property.Cash flow is the income (rent) minus all expenses: mortgage payment (including principal, interest, taxes and insurance), average maintenance costs, capital expenses (new roof, hvac, water heater.

Here in Reno, NV there are some cash flowing properties but we have a strong appreciation and equity building which is where you will build more long term growth.   

- Time horizon- Cash flow vs Equity vs hybrid- Passive or involved?

It's got a lower entry point, and the cash flow tends to be pretty sweet.

Property taxes can be a huge impact on your cash flow based on the city you buy in. 

But in reality you need to worry about cash flow.