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.

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

@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. 

I’ve just joined with the annual pro (or pro annual?) 

In order to past this SS test, your appraised market gross rental income at 75% has to be more/equal to your monthly mortgage payment (PITIA).

I have a salary and a good amount of real estate income.So far I encountered issues as my real estate NET income looks like $0 because of depreciation, and so the DTI looks inflated since I have the corresponding real estate debt.I am looking for 300k HELOC on $1.2M property with $660k mortgage at 3%. 

Based on my projections I assume I would earn a negative cash flow between $400-$1,000 annually lol. 

This is a business-purpose-only loan for real estate investors that allows you to use the projected rental income to qualify.

.; rent medians and lower and upper bounds, typical days on market before securing a tenant, local vacancy rates, tenants' typical income, education level, employment opportunities, credit, and rental history).