I worked with one and that experience is the reason I now own my own PM company. 

This experience taught me to trust my instincts more and never skip due diligence, even in areas I am less familiar with like basements and water intrusion.Any advice on how I should proceed would be greatly appreciated.

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?

Anyone have experience using Turbo Tax Premier to do their taxes having investment property(ies)

I work with a lot of househackers and they're typically on the 12 month cycle, rinse and repeat.While the proposition of acquiring an investment property outside of your market in a "landlord friendly" state may sound appealing, i would recommend you stay local for now and househack another couple of properties over the next few years until you've got some more time / experience under your belt.you would need a management company to cover your property that is outside of your market which would not only take 8-10% of your gross it would also leave you a bit vulnerable to a property management company that you A.)know nothing about and B.)you won't have the experience or cashflow or proximity to deal with any headaches that may arise.i would recommend staying local and househacking your way along for now and then maybe hire a local property management company initially to work with your current/local properties to get a taste of what to expect if and when you begin investing outside of your market.

I have rented out this home short term before and have been successful but I don't have any experience with 12 month leases.  

Hi Karla from Montreal, Canada-You ask an interesting question.Should your first real estate investment be new construction, since you and your partner have construction management experience, or flipping an existing home as you originally thought you would?

Any insights/people with experience in this market who can chime in?

I know when it comes to many cities there are long permit processes and also there are specific air laws that go into each city.I would love to hear a story that goes over an experience pertaining to developing/rehabbing a property in the DC area. 

Quote from @Shaun Ortiz: Hi Jason,Thanks for sharing your journey—it sounds like you’ve gained some invaluable insights from your experiences, even with the squirrel tenants (that’s definitely a story!).