Both the tenant and landlord should be reminded at least once or more per day, ideally not just by email, but also texts and canned telephone messages.I became of aware of this flaw recently when I was in the middle of difficult overseas travel and the ensuing recovery from jet lag and failed to realize that a tenant had not paid until the end of the month!  

Of course my other information (email, phone) will be on the postcard, but ideally they go right to my site for a response.

The water issue is fixed but they informed me during the winter when it’s not ideal to paint. 

My goal is to regain as much as our investment to date and ideally break even (but likely be slightly under) and keep it a fair deal for both of us.

As such, I'd look for private money/bringing in a partner (ideally someone who is more experienced) to help fix and flip.

I am trying to improve mine though, because it is ideal to get your properties into a stable, long term loan.

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.