But as it stands I think you've already made the choice.

This is what I would consider a stand up triple in my market (hope you like baseball references).

@Dorys PrenticeIf the little hairs on the back of your neck are standing up, do whatever you need to do to protect yourself.

I like to send letters that I fill out the address individually, which has helped me stand out.

Which made me stand out out of over 25 showings that day.

I know you stand to make $70,000 profit on the sale but since you are upgrading your home in the same location you are essentially realizing no gain since you are going to sell at the top and buy right back at the top on the second home.

So I could stand the expense if I could be assured this was a good long term investment.  3) I thought of refinancing, but paying longer on the house doesn't appeal to me. 

If so, then I’m pretty familiar as I own two duplexes, one on Liberty St and one a block from Liberty in two different parts of town. 

You stand to gain a lot of money, but you must also be aware of the risks if you want to cut corners.

Either of them will probably be able to insure you at a lower premium than a stand alone Umbrella policy.