Getting started with out of state buy-and-hold properties

[Richard S.]

Hi everyone,

I am an investor here in Chicago, currently in nine properties. Two are buy-and-hold and seven are short-term debt. The competition is pretty fierce for cash flowing properties so I've chosen this strategy to offset the cash flow from the debt deals with the tax benefits from the rental properties. The problem with this is that the debt side is inherently short-term (2-3 years), so those deals need to be constantly replaced.

I've decided that a better approach would be to consider out-of-state, cash flowing buy-and-hold properties. There are a few smaller cities I'm interested in, including St. Louis and Nashville. 

I'm wondering how big of a leap this is from where I'm at now, how to get started, common mistakes, and maybe what to watch out for (legal or tax issues, etc).

Thanks,
Rich