@Roger Hefner  I tell fellow Veteran friends to look into becoming a landlord to supplement their income.

We are looking to supplement his future teaching salary with outside income through real estate investing.

Here's a first stab at a list for those of us that aspire to be competent and confident in the realm of personal finance: Less than a month: Emergency - one bad day from homelessnessOne to three months: Urgent - a moderate amount of bad luck from homelessnessThree to six months: Whew - The baseline of being able to sleep soundly at night, still in all-out hustle modeSix months to two years: Satisfactory - no longer afraid continuing to support one's self/family if job/business is lostTwo to five years: Well-off, Investments are just starting to produce meaningful amounts of supplemental incomeFive or more years: Confident - Investment income may be even more than most people's salaries25 Years or more: Financially Independent - even with the conservative 4% Safe Withdrawal Rate$100,000 more passive income than one spends to support their lifestyle: Wealthy$500,000 or more in passive income above and beyond what's needed to support one's lifestyle: Ultra WealthyThoughts?

He told his wife they didn't have any money but she went out and spent $800 on supplements and getting her hair and nails done along with a few other things.

My wife and I try to supplement as much of our living as we can through Costco.

While the cost of actual ownership due to interest rates may be lower than historical averages, you still need to get there first and purchase the house.My attempt was/is to supplement your analysis. 

This info will give you a decent idea of what to expect and help filter down your search to a few cities.Some of the metrics that I find valuable to understand are:- Population - Home Values- Household Incomes- Rental Vacancy Rate- Homeowner Vacancy Rate- Poverty Rate- Educational Attainment Rate (High School/GED & Bachelors)- Number of Housing Unit- Rent to Income Ratio- Rent to Price Ratio- Population on SNAPS (supplemental nutrition assistance program) percentage- Property Tax Rate- Median Age of Buildings- Number of Structures by Units (SFR, Duplex, Triplex, Quadplex, etc...)- Median Rents by Number of Bedrooms- Unemployment Rate- Employment Sectors Percentages These are just some of the indicators that will help you understand the quality of an area as well as the kinds of returns one is to except.

I really want to find a way to supplement my income but I don't think New York is the right state to do it in.

What is tenant doing (planning to do) to supplement income if they expect to have income loss?

I hope at some point, I'll be able to supplement my income with real estate and just add to my cash flow line.