My known options are hard money or private lending and then maybe doing a cash out refi, but rates would be high on both ends and will really cut into my cash flow. 

Fellow Iowan as well.

I live and invest in Milwaukee since 2007, so probably a little bias here, but we are set up very well for future growth. 

well, there are gurus and wannabes that's for sure, but if everyone did some research they could figure that out and get the right people to guide them.

We are looking to buy a condo in Chicago as the new rental, for a variety of reasons, but most importantly because it would rent better in the city, and it fits our desired price point (so we can allow for the rest of $$ from the sale for paying off their Oregon home and pay all, or some of the taxes on the boot). 

You would probably get a variety of answers even from tax professionals.

The migrant farm worker program works fairly well.

I have been in the books and came accross Bigger Pockets, i would like to dive head first into real estate investing but the un known is a little scary.

I am glad things worked well for you over the years. 

For me, the permitting process with Delta went well.