As far as it predicting high on revenue, that's obviously the biggest risk and I'd be concerned about that as well when getting into a new market as a short term rental investor. 

Trying to nail in a location that will have high volume of renters.

Great time to expand values are high, rates are going to start to fall again in the next 60-90 days.

I have heard interest rates are quite high there. 

I would highly recommend working with a broker that really understands the nuances of this style of loan as each lender has different credit requirements, leverages, and ownership requirements. 

Just finished the book how to invest in real estate: ultimate beginners guide.Also, could I ask help from you great realtors here on evaluating my first investment and do you think it would be a good first step?

Even if it took 2 years to build (which the builders have a very good historical track of finishing within 14mo on much larger projects than this, we have funds to cover the carrying costs.

The second property will be purchased with a mortgage (you can determine how high or low the leverage will be by adjusting the proceeds you use or the price point of the 2nd replacement).You are adding some measured debt at a level that your dad can be comfortable with. 

If you're looking for more connections, I would highly recommend attending some local real estate meetups in the cape cod area.

MICs generally charge a lot in points and have high rates, and typically won't lend above 75%-80% of purchase.Some brokers will also have access to private individuals who are willing to lend, which can be more flexible.