I won't be able to make the cottage legal rental without living in the primary home myself.

We also have a nextgen in our primary home that we rent and collect all rents for that to the same account as the rental.

We got both primary auto and umbrella insurance on it.  

The biggest challenge is a lack of quality homes and a rapidly increasing demand for vacation, second and primary homes.

Curious to hear others thoughts: Do you believe experience is the primary factor, or are there other qualities that matter more?

@Bobby Short Depending on the equity you have on your primary residence you might be able to find a lender to finance the property in CR with your primary residence as collateral.

The primary risks at this point would be       1) to your lender, the risk of a margin call.       2) To you; underestimating the true cost of a project and cost overruns      3) To you; legal risk of securities regulations if you partner looses money. 

When I return to the country after my Au Pair contract ends, I hope to live in the property as my primary residence and house-hack as well.I understand that investing remotely makes things more challenging, but I am also ready to be uncomfortable and challenge myself in this journey as I know it is 100% possible.

It’s actually in Frankfort, IN and bank was Centier only because I had my primary mortgage through them.  

You could do something like what you want if it was your personal primary residence and even then the interest rate would be ugly.