Neighborhoods like Logan Square or Albany Park have seen growth in rental demand, making them potentially good starting points.

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

A short time later, I found myself on a plane to Spokane, Washington, to attend an Inner Circle class which was taught by Lee Arnold personally.

You don't necessarily need to invest in WA in order to be closer to home.

Based on the tenor of your posts, I've got to ask - do you have your primary residence squared away?

As to the buddy I mentioned in Washington state it was the same scenario; he converted tax-free up to their standard deduction but above that he kept within the lowest tax bracket and paid the smallest amount of tax possible.Thank you @Basit Siddiqi for calling me out on this and giving me a chance to address my mistake; it's important people have the correct information.  

We don't own any properties in Sheboygan, the furthest north is Port Washington and that has been great.

If it was me, I'd just go conventional or use a vacation home type loan w/ a lower downpayment. 

For example, this can be adding square footage, adding an extra unit, or adding a pool in a STR market/luxury market.  

(And - full disclosure - I will be using a mail forwarding address also and only occasionally actually hosting meetings at that location... it's like a 'WeWork' space, I generally work from home and my managers are on-site at the parks...)To everyone's continued success, and due diligence,-jl-do you know the Taylors I think they are SF based I sold them one of my parks a decade ago.. it was in Vancouver WA..