Do sunshine and beaches matter more, or a strong job market in your specific field?

Mailchimp also I believe is free up to a specific number 

Are there specific military programs or contacts I should look into for housing opportunities?

Multiple investors with decades of experience, some GP, some LP, some skeptics about the entire business in general sense and some bulls who have gotten rich from investing have all chimed in on this you got links to specific case studies from Brian Burke, a seasoned syndicator, a guy check from Melanie p, who makes it a part time job taking the trash out and exposing the shenanigans of one syndicator after another.Greg Scott has an excellent reputation on these forums, and provides a counterpoint to Melanie’s skepticism.

Reason for asking is that I am trying to understand what a reasonable target rent per unit is for specific geographical areas. 

Are there any tools, websites, or resources you’d recommend specifically for real estate investors in Ontario?

Rent control laws are market specific.

Just trying to gauge whether your bookkeeper is overcharging, especially if you are splitting duties.I would be careful with real estate-specific software.

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

Real estate transactions, especially flips, come with specific tax implications such as the potential for dealer classification, short-term capital gains, and cost allocation for renovations, which can significantly impact your tax liability.