It’s personal to the employees, who are directly impacted by the work culture of the business and rely on it as a source of income.

Property taxes, income taxes, sales taxes, declining population, unfavorable rental laws, winter weather.

Previously I'd always used Stessa, which has a great Net Cash Flow statement view, breaking down the usual income/expenses, but also includes a section for Interest/Principal, and another section for CapEx. 

For quick math I have a range of each between: 700/yr to 3% of gross income

It's going to be tough to buy a property without steady W2 income.  8k is a good start, but you might need to keep saving.  

My answer is always a mix of: You’re overthinking it and work smarter, not harder.A lot of investors are sold on the idea that STRs are a passive income source—which, to an extent, they can be.

For context when we do this our biweekly payments have been around $485 per paycheck so around $1,000 per month of lost income per person when we both do it. 

I've seen some people house hack a single family home by renting out the rooms, but keep in mind that traditional lenders would not be able to use the income from renting out the rooms (known as boarder income) towards additional income on the application.

I don’t know if I should invest in the Jersey market and put maybe 20-50% down on something, make less cash flow and make more appreciation, or every two years or so maybe buy something fully cash (my own $) in the Midwest let’s say 5-10 units and make more cash flow with no debt as with the income I make I can just save and buy more, don’t necessarily need to leverage in some markets.

Here's why some choose bricks and mortar:Tangible Asset: You own a physical property with potential for appreciation.Leverage: Use debt (mortgages) to magnify your returns (not possible with stocks).Passive Income: Rents provide a steady income stream (dividends are not guaranteed with stocks).