I've owned and managed my own rentals for a little over 13 years now and dishwasher troubles pop up from time to time but in my experience, the most frequent issues arise from garbage disposals and tenants being too rough on them.

Every single person who I know who has succeeded investing remotely fits in this category: they have experience already and used to live in the market they invest in, or travel there frequently enough to know it on a block by block basis.

Leaving it in the STR can actually be a win-win—it saves you on initial Airbnb setup costs, and guests won’t know the history.

How can I position this as a win-win to the seller while also giving me flexibility to either rent it out or resell it later?

They aren't being lazy, they know this is no win.  

Nothing fails like success, and stupid loses more than smart wins.

Not close enough to win winter STR guests, but totally feasible for your own use.The whole are is within 6 hours of Chicago, about 4 hrs from Milwaukee and Twin Cities. 

Numbers that spell out a win-win for all parties can be shared on a cocktail napkin...

As Sam Williamson, Senior Economist at First American, says:“A home is more than just a place to live—it’s often a family’s most valuable financial asset and a cornerstone to building long-term wealth.”Bottom LineReal estate isn’t about overnight wins.

What kind of reports will I receive, and how frequently?