The biggest thing I'm seeing actually isn't his residency status, but I think you'll have the biggest issue with the value of the properties you are looking at.

One of my biggest questions is could I sell that second house on its own once it's built?

The term "investor friendly" is the biggest joke!

This is something we had to do in order to comply with the soft story earthquake retrofit work that required the displacement of a renter to make structural improvements.Regarding @Amit M. comment. 

This is the biggest mistake we have ever made.

I think the customer service, amenities, and ability to make the stay stress-free for the guest are the biggest advantages once you are booked.

When owning a vacation rental, the biggest financial risks to you are from fire, water, and liability.A solid overnight rental insurance policy will cover you for all of these risks.

Get as much understanding and disclosure as possible on the closing fees and escrows that will show up on the settlement statement - including stuff like prepaid interest ("stub interest"), tand and insurance escrow holdbacks, etc - biggest pitfalls we've seen are people not 1000% clear and aware of these things then getting very negatively surprised at the day of signing 

What are the biggest challenges you face as a private money borrower?

From PA, my biggest challenge is using the 1% in these areas of Monmouth county.