Charge the $99 for $5K coverage and $500 deposit directly from guest (these are million dollar homes).

Unless you are a professional athlete/movie star / influencer it’s hard for many to hear this but the world really doesn’t give a hoot about you.Having built hundreds of multimillion dollar homes and having worked on projects with two different professional sports teams owners - I would say less than 1% would use a land trust for anonymity and some of these people had 9 figures and several were billionaires.

There are multiple billion dollar companies dumping money into the city, such as Intel, Google, Honda, and Amazon.

It does not cash flow now with the increase but if I raised the rent it would cash flow a couple of hundred dollars a month (the home is paid in full), at this point I'm losing money (between the tax increase and repairs)Are you betting on appreciation in your investment strategy?

Im happy to mention real dollar amounts and share more about what I've seen! 

In the end there was a multi million dollar renovation that caused many families to have to sell their units.

I personally have dumped thousands of dollars in renting these units over the years and have seen townhomes filled on a weekly basis.

Whoever is buying these for 90 cents on the dollar and having to go through a BK before foreclosure is going to lose their shirt on these assets. 

If you're spending your time counting trivialities like this you are "tripping over dollars to pick up pennies".

It will save you a couple thousand dollars in financing costs.