Setting up portfolio for early retirement

[Angela Costa]

I have 3 SFH's and 2 townhouses as buy and hold rentals. Paid off primary house. Have a property manager. Current plan: working W-2 job around 140-160k/year. Maxing out retirement accounts, ira, adding to taxable accounts (index funds) for pre-age 59.5 access. Current age 40. Goal: to have enough to retire by age 50 from cash flow from rentals, stocks/bonds portfolio. I will get a small pension at starting at age 65 around $1000/month. But it may be $1700-2K/month as I am still working at the w-2 job for likely another 10 years. My rentals have between 60-100K 'dead equity ' each but with mortgage rates 3-4%. Would you sell one to pay off another, cash out refinance ( was quoted 7.5% rate), or just continue to hold until maybe cash out refinance rates go down? I was thinking option 3 made most sense and also not sell any of them since they cash flow and have been able to get new tenants fairly easily or have had long term tenants. For reference: I acquired all 5 properties in year 2020. I have an idea of taking cash out refinance with VA loan (partner has benefit) and rates look to be 5.75% on primary home (owned free & clear). Can you give me direction of what makes most sense given my long term plans? I don't actually need the cash flow until late 40's/age 50. I have low expenses. Maybe just keep doing what I'm doing until rates favorable and I have desire to reduce my w-2 hours. I have a flexible schedule and can work less or more hours.

[Jeff Nash]

You have a lot of information packed in here, and a more aggressive retirement age goal.  Your fact pattern appears very encouraging and positive.  Your biggest risk if you execute the plan will be running out of money in retirement, either due to natural longevity and/or later health issues draining your resources.  That is an inherent risk to everyone, but especially early retirees.  For the property analysis and decisions I would chat with someone like @Denver McClure.