My endgame is to end up with $300k/yr in post-mortgage income in 20 years based on investments I make now followed by continued investments over the next 10-15 years own.

I’d also recommend getting a few quotes, including at least one from a mortgage broker.  

I think I have paid my full mortgage with the money paid out by Homeroom twice in total, every other month I have to pay out of pocket.Similarly to another poster I had both the laundry machines provided by Homeroom break on me, then on the second one when I asked why they both broke so quickly they indignantly replied that it's 12 years old you know, these things usually only last for 5 years or so, meaning that Homeroom sold me an 11 year old washing machine and then blamed me for that.

Two, you'll have a much easier time obtaining a mortgage product if you have a track record of W2 income.In the meantime, continue implementing the strategies you mentioned: save religiously, build your credit, pay any existing debt owed, etc.

Have a 27k mortgage balance, sale price est at 415k.

Mortgage lenders will qualify you for a higher purchase amount for multis than they would on a single, because they will count the rent you will be making on the other units as additional qualifying income for your loan application.

Time overcomes low cash flow to some degree... rents go up while your mortgage stays the same and your tenant pays down your mortgage.  

I dept free minus these mortgages.  

., Purchase Price: $475,000 ($197.9/sq. ft.).Estimated Market Value: $402,000 ($168/sq. ft.).Financing Terms: 2% interest rate, with a 9-year balloon.Unit B Income: $2,049/month (Section 8 tenant through November 2025).Unit A Income Potential: Similar rent or higher; Section 8 cap for the area is $3,234/month.Monthly Loan Payment (P+I): $1,386.Cash Flow Breakdown (if both units are rented at $2,049/month):Gross Rent: $4,098/month.Vacancy (10%): $410/month.Operating Expenses (37.3%): $1,376/month.Net Cash Flow: $943/month.Key QuestionsWould you be comfortable paying an 18% premium for financing at 2%, especially in a market where current mortgage rates are closer to 7%?

Home equity is the difference between what your house is worth and what you owe on your mortgage.