In the beginning stay away from complexity-auctions, land contracts, FSBO etc.

We would looooove to house hack but seeing as it’s so expensive to buy in Brooklyn and we aren’t going to stay here long term, it doesn’t make sense for us.

That could be a great way to find and stay engaged with local investors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors and agents in Chicago and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersBest of luck to you and look forward to following your journey!

I feel like it's not that long but also feel like I'm not getting a lot of luck with quality people.You are coming into a tougher rental period but i think your mindset on triggers to stay competitive will help.

I reject all “hotel” bookings for 1-3 nights more than 2-3 weeks ahead because I always try to leave open for a longer weeklong stay or to rent the place to a signed tenant on an ongoing lease.It depends how much your time is worth.

That could be a great way to find and stay engaged with local investors, realtors and opportunities. http://www.biggerpockets.com/alertsYou can also search for other investors or brokers in Huntsville and follow their journey on Bigger Pockets here: https://www.biggerpockets.com/search/usersAnything you can do to build your network in the region will help you find the realtor, and eventually the property, that suits your needs. 

The existing tenants stayed and they have been great.

She stayed up all night with various people here on BP, arguing that I was possibly the world's crappiest person. 

Does the location stay the same?

What might need to learn how to raise money and form Partnerships where you stay in control.