@Hideyuki GojimaI would tend to agree with you on the insurance side when it comes to a claim filed by the policy holder. 

If you are in the 24% tax bracket, then for every $100 in interest you pay the mortgage holder, you save $24 in taxes.

Also will most likely need to find an accountant as well at some point during my journey, but I am lucky to be US passport holder which should make my adventure easier.I am open to hearing all advice through replies or private message is fine aswell.Thanks

Or do all hard money lenders required to be 1st lein holder on all properties?

So, I have multiple Sub2 Properties, but I have noticed that later down the road the Seller (Mortgage Holder) wants to obtain a new loan to purchase another property and needs a letter or document showing that we are now paying the mortgage in order to prevent the mortgage from counting against their debt-to-income ratio.

Great for the tax lien holder.

Everything started with me funding a fix and flip project in Washington state as a junior lien holder.

The first lien holder will be ahead of any judgment against you.

The boy is from Latin America on a tourist visa here.

Stay for at least a year before doing this again (a year to satisfy the new mortgage holder, or 2 years to obtain the capital gains exclusion for tax purposes).