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

Even if it's the biggest unit, you need to move into that one to satisfy the mortgage if it's liveable and then figure out how to get the tenants out.Who was your agent on this because they have not prepared you for anything? 

The term "investor friendly" is the biggest joke!

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

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 

One main downside that I see with syndications is the fact that they don’t provide ongoing long term dependable cash flow, which is what I really am aiming for if I want to be able to afford to cut down my hours.

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.

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