I am moving to Oahu with my girlfriend and we want to take this opportunity to transition from renters to homeowners and from consumers to investors where through house hacking we would end each month cashflow positive.

This has been our exit plan to transition to fewer doors.

A good broker can help you with both to make the transition as seamless as possible. 

In fact, I've changed basically nothing from the strategy I've been running there since 2019.That said, I'm strategically picking properties in strong C Class areas that have potential to transition quickly to B areas.

However, a challenging situation has arisen: the previous owner's son, who lost the house to the bank, is currently occupying it.I've attempted various methods to facilitate a smooth transition, including offering cash for keys and assistance with moving expenses.

They are proposing some sort of transit about a block down.

My intention is to establish positive communication with the current tenant while respecting their existing lease agreement, with no plans of requesting them to vacate.I would greatly appreciate any insights, suggestions, or advice you might have regarding reaching out to the tenant, drafting a letter, and managing this transition smoothly.Thank you in advance for your assistance.Best regards,

Now, I have transitioned into wholesaling mobile homes.

This in essence to pull liquid cash out for a second investment, and transition the property into a long term rental.

Your situation is unique and presents an exciting opportunity for your retirement planning.Given your aim to maximize your monthly income to supplement your CalSTRS retirement fund, and your desire to continue investing in properties post-retirement, here are a few suggestions:Assess Your Risk Tolerance: Transitioning from California properties to Indiana duplexes involves a shift in market dynamics and possibly different risk profiles.