@Beck DeYoungNegative cash flow in real estate investing can be attributed to factors like low down payment, high housing costs, and poor expense accounting.

In comparison to annual MLS dues, the cost of obtaining an NMLS license is negligible, and more importantly the value of expertise it provides  clients is net positive investment for time and expense.

This question verifies the tenant’s responsibility in managing household expenses.

For example, should I have one checking account that manages all expenses, such as down payments for properties and serving as the main source for rehab budgets?

To me cashflow is important to cover unexpected expenses but I buy for wealth creation and tax benefit, not to supplement my income.

Also, make sure you have an emergency fund to cover six to twelve months of expenses before you buy a house. 

I grew up here and when I came to the city as a travel nurse this summer, the month to month furnished rentals were outrageously expensive, $4000-$5000 a month easily to be in a nice building anywhere in River North, Gold Coast, Lincoln Park, West Loop etc.

With respect to your 2 questions, 1) when you sell the property, all the depreciation taken (regardless of whether it was used to offset income in the past) is subject to recapture.2) You can reduce your taxable capital gain by subtracting the selling expenses from the sale price.

If things don't go as expected, an eviction is quicker and less expensive than a foreclosure.

That's a healthy expense.