Looking for advice/guidance on general RE investment strategy

[Jon Gorman]

Hello,

A bit about my current situation: I own my current home (currently paying down mortgage, 2.9%). I have been renting out my previous home and with the rent I am collecting, I am netting approx $500/month on top of the mortgage (3.75%) and other expenses. I also have a commercial office space (5.25% mortgage) that I use as my office and rent out other offices in the building for some passive income.

My goal is to retire as soon as possible, which I define as having enough passive income from investment properties to cover my living expenses. This will happen one I pay everything off (both investment properties) as well as my current home. If I pay everything off paying only scheduled payments, I have about 15 years left on both investment properties and 30 years left on the home I live in (we just moved into it within the last year). But, if I pay off the mortgages more aggressively and snowball to accelerate payments once the first property is paid off, I can have everything paid off in 10-15 years.

My question is: How should I think about strategizing reaching my goal as quickly as possible? Should I prioritize paying down current mortgages as fast as possible with any additional income vs. leveraging investment properties to buy an additional property vs. selling our old home to trade up (e.g., buying a vacation rental in a high-demand area)? How would you make this decision?

Thanks!

Jon