We have also had issues where the occupant filed for BK and they were able to stay for 1 year and it cost us 10k in attorney fees to get them out.

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

I have a great realtor, who understands investment property and to my knowledge exists solely in this space.

I am looking for advice and knowledge on how to go about getting into a second deal with all my funds tied up in this duplex currently.  

I asked myself that as I proceeded to iterate and categorize my knowledge into the "what I have a decent understanding of" pile and the "yeah bud...you need to learn more about me" batch.As soon as I started this culling process, Thee Answer slapped me right in the face!

In order to overcome the problem, the Turnkey Company would do well to, at a minimum, invest in having a 24 hr number where someone knowledgeable, actually picks up the phone by the third ring and can answer questions and deal with problems. 

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.