Ideally we'd find a property between Minneapolis and Birchwood that we could use while visiting and STR otherwise. 

The benefits of ownership are HUGE  I just want to say I really really really like this answer.So when I deal with such-and-such "financial advisors", usually I dig up their past thru linked In or social media or any other stuff to check their credibility.

One of the challenges you'll face as well is the car aspect - going to view the property or running in to any maintenance issues so would ideally need a 1) a real estate agent who works primarily in these areas who knows what you are looking for and can do viewings for you and 2) property management company or a good reliable relationship with a handyman.

Would love to jump on a call ideally.

I want to be as confident as possible that a well-managed STR in my location will be able to at least break even (covering mortgage/taxes/expenses) and ideally provide a profitable cash flow.

@Shelia Stokes, an experienced coach/mentor should ideally have an established business that grows and performs year after year.

@Jack Seiden, we'd ideally like to rent the entire property rather than room by room, so perhaps a Condo or TH makes more sense?

Young professionals, baby boomers, and residents who "treat my properties like a HOME" When you start with the end in mind you end up with a portfolio full of properties that will attract your IDEAL resident.

Ideally something that can:- manage scheduling, with multiple properties to clean/flip- communicate with cleaners- offload manual workNote - I use Hospitable to manage my Airbnb/Vrbo setup, but I'm talking something I can set THEM up with to better scale their cleaning business.

That would be a perfect move for HELOC money in my portfolio, as it wouldn't max my line, and the goal is to repay after improving the property, ideally under a year.