Your DTI max is 43%, so with being very negative on cashflow, that means your regular income would need to be able to support it but at least the option is there. 

You can have someone bring in an adequate generator to test whatever you feel the need to test.

As you know, it is really hard to have possive income immediately.

As the title suggests, I'll be living there, while renting out the bottom portion for income.

Additionally, the potential for value-add opportunities such as adding a ministorage or other high cap rate investments in the future could further increase the overall return on investment.Considering the potential for appreciation, the current NOI, and the future potential for additional income streams, this property could be worth considering as a long-term investment, despite the initial lower cash on cash return.

Has anyone used awning.com to estimate income on short term rentals to analyze a deal? 

Between the four 1b/1b units, the property generates $3,800 in total rent, and all utilities are paid for by tenants.

@Nate P.Your profile hints that you are living abroad.If you are a US citizen - you want to make sure that the CPA you work with understands the foreign earned income exclusion(FEIE).If you purchase a property and are expecting valuable feedback on how that property will impact your tax return, you will need to provide a rough profit and loss projection(rental income and expenses) along with purchase price to have a conversation with your accountant so that they can provide you good feedback. 

While navigating these alternatives, you can gain STR market experience, build equity, and potentially generate income to improve your credit score over time.

One thing to consider before looking into the cost segregation is to see if you would be able to use the loss generated on your tax return.