My wife, Stephanie, waits some tables and supplements our income for extra spending.

Patrick, there are basically two types here, those that make their living from real estate activities and those that supplement their income.Not necessairly an active/passive position.

Do you want to cash flow, retire from your current occupation, make investing full-time or just supplement your current income.  

As someone that is looking to buy their first investment and doesn't need supplemental income (also doesn't want a negative ROR) should I just bite the bullet and just shoot for a $1 cash flow and bank on appreciation?

It may not give you a supplemental income, but since you are young and you don't really need the income right now, this could be a great long term investment.

I am looking to acquire rentals to supplement retirement income in about 8 years Honestly -- I'm not that old.

I am looking to acquire rentals to supplement retirement income in about 8 years Honestly -- I'm not that old.

My income and expenses are such that with effort I would only need to supplement my income by a few hundred dollars per month in order to reach my goal.

Mom only pays taxes, insurance, HOA...Or refinance conventional depending on her income and use for temporary money and rent the house to supplement.

The person gave a complete application, but failed to also provide the required supplement info such as proof of income (pay stubs and such).