My partner and I are eager to embark on our first real estate venture by acquiring a long-term rental apartment in downtown Chicago.

State Auto assured me that my insurance premium wouldn't be affected because there was a zero-dollar claim.At the end of last year, State Auto was acquired by Safeco, and my insurance premium increased by around 190%.

I am sure she is sending him letters (or using other methods to contact him) as well.I'm a small long-term buy-and-hold investor myself, but this property is about 4 hours away from my own market, and would be used personally by my wife and I if we were to acquire it.I'd really like some help from you large operators who work these deals all the time, as to how best make contact with the owner and see if he were interested in selling.  

My best rule of thumb is to have 20k for every 100,000 on the property I am soon to acquire.

-Zach, those coaches are employees of our investment company and have played a huge role in the 2,000 + units we've been able to acquire.

However as a general rule of thumb when the lenders begin to nudge you when you are operating smaller assets single LLC's, its usually time to begin acquiring in a separate LLC.I don't want my comment about having separate management LLC's to be construed as having separate deed holder LLC's.

This is a very easy way to keep acquiring properties.

I am also looking to connect with RE agents in the area to gain a better understanding of what is currently on the market and how these types of properties fit into the Tampa area.I'd like to also acquiring any insight into current supply trends, as well as the demand based on occupancy for these types of properties.

It would also lessen my out--of-pocket on either hard money costs or cash I spend, so I'd have more to work with to acquire more properties.

So, as a technology entrepreneur, I got to wondering if there's a way to research, acquire, and manage my deals more easily using the power of artificial intelligence (AI) or some other internet software.I have an idea of what I think I need to build, but before I build it, I would appreciate some feedback from this community: What's the hardest (or most frustrating) part of real estate investing for you?