One challenge to manage is being able to clarify for lenders on those rentals (if you have them) which amount of the premium should be paid for each rental so that they do not include the entire premium into their escrow analysis, inflating your monthly payment on that rental. 

There's a good chance we see more details on his proposal in the coming months. 

I reconcile our trust account each month in about ½ an hour.

We want our kids to be able to be close to our families, so ideally, we visit Oahu a few months every year.I spoke with a few realtors and it seems like the best investment would be the condo hotel as they are legal Airbnb/STR.

We plan to keep them on a month to month lease but after a few months, have them sign a year lease and increase rent, however, we need help finding a GOOD app/website to get lease agreements/documents from or get a template so we can fill/add certain things we want.

I am not a tax professional trying to sell you my services I am simply providing my perspective. 

A bit pricey if you do only a few flips a year, but I'm going to give it a shot and seems if it's worth the monthly cost. 

Rather than paying for childcare services from a large organization, we found that it was significantly cheaper to pay for a second mortgage than to pay for childcare.

He casually told me he sends out 10,000 pieces of mail every month. . .ten thousand!

  $6k per month and $30,000 to get it going and it cash flowed about $20k a month.