Quote from @Dennis Bragg: Hi Breeya,You’ve got a killer set of strategies already!

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

Sounds like you’re in a strong financial position, and it’s clear you’ve put a lot of thought into your strategy. 

That's not a great strategy for Danbury.

House-hacking in a multi-family unit is one strategy I wish I had been aware of when I chose to purchase my first property.

However, part of our strategy is to build a property management company that specializes in working with subsidized housing programs.

If you were in my shoes, what real estate strategy would you recommend for scaling quickly (but smartly) so that I can replace a good portion of the W2 income from real estate investing?

What changes did others incorporate into their leases that were influenced by this years tenant interactions? 

When investing in real estate, having multiple exit strategies is key.For a single investment property, make sure the numbers work for both scenarios: 1️) If you decide to sell the home, the deal should produce a solid return. 2️) If you need to rent it out, the rental income should cover expenses and provide a profit.Flexibility is what saves you when things don’t turn out as planned.

It’s a tough decision, but we’re adjusting our strategy to align with market conditions and our timeline.Having come from a corporate background, I’m used to doing these kinds of planning exercises.