I have a long-term rental in STN MTN (Stone Mountain) GA, and have a one year lease with a section 8 tenant and content with the cash flow, however, I can make more if the basement gets converted to a separate unit.

If you had small losses (no past due tax payments) and the late return penalties are lower than the tax prep fees you saved by not filing - you come out ahead, but it’s a win with an *.

Hold time and cash flow expectations 5.

I am basically the traditional Asian family that spent my entire life saving money and purchasing a place in New York City, and after trying to survive for a while I find it too hard now that it’s 2 people and decided to move back to my hometown and do some investing looking for cash flow in particular.

Plus, I want to increase my portfolio as much as I can for the cash flow because I'm about 4 years away from retiring.   

Looking to utilize the BRRRR strategy for my upcoming properties to build that portfolio of cash flowing appreciating properties!

The less risky/more logical avenue seems to be to LTR one unit for more predictable cash flow and STR the other unit to create availability for my relatives when they come to visit.

I am guessing they do everything including cleaning themselves and must have paid all cash.  

It will also depend on the amount of capital you invest, if you buy in cash most properties will cash flow.

When you look at the illustration, the 1st year Cash Value should be 85-90% of the Premium.