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.

What is the risk tolerance that’s required in Dave Ramsey’s portfolio to achieve the returns that will grow his assets enough so that just a 4-5% withdrawal rate in retirement will suffice his supplement income goal in retirement?

You can argue that nobody stays on welfare for $1,000 a month but the truth is there are a lot of people that take that $1,000 a month and then spend their free time hustling for cash, dealing drugs, or otherwise supplementing their lifestyle without Uncle Sam knowing.I used to work for the state.

Have my home free and clear, have a family lake cabin free and clear, be able to take 2-3 months off every year during the holiday dead season, and eventually generate $40k+ / yr in semi-passive rental property income to supplement the cyclicality of the business!

You asked for tips and tricks so here’s one that probably is going to sound completely crazy and very slumlord-like but I’ll post it anyways .when a tenant in these areas move out they usually leave the place a wreck and it needs carpets cleaned ( I use 68 cent a foot brown office carpeting ) and painted ( I use gladden generic semi gloss speedwall 16$ a can) what I do is go ahead show the property to a prospective tenant anyways and when they arrive I have a bottle of windex out a rag a broom and inform them I’m working on it .

Right now I have been looking into starting a supplement company focusing on small batch high quality protein powders and pre work outs with a military theme but not really sure so I’m just seeing where 2020 takes me and I’ll figure it out as I go.