Some questions to consider:1) How much negative cashflow can your other income stream(s) support?

My plan for this year is improve my credit, get my real estate license (to increase my income on top of my W-2), possibly career transition into the property management space (to learn more), and save as much as possible and learn as much as I can.I’d love to house hack close to home but my area is so expensive it seems like it’d be close to impossible. 

Quote from @Jeffrey Bourque: Hello All, I am new and this is my first attempt at purchasing a property with the intent to create monthly cash flow.The property: Triplex Listed at $140,000 - Total monthly rent income $2,150 - Tenants want to stay and are all willing to sign new leases for 3 years - 8 beds 5 baths and 3,500sqft livable space on a 4,800sqft lot - Heat and electric paid by tenants and water trash paid by owner $180 month - I have managed to talk the selling price down to $105,000 with a kick of $10,000 for closing and commissions so $115,000 all in - Building is in fairly good shape according to pictures and questions but have not done a inspection yet - some general maintenance repairs are needed according to the seller but nothing that seems to bother the tenants. - Taxes are on the higher side at $6,000 yearMy Numbers: $115,000 putting 20% of my money $23,000 and finance the rest with total expense of $1,834Monthly expense numbers: Future Maintenance 13% $273 - Vacancy 5% $105 - Property Insurance 5% $105 - Property Taxes 23% $500 - Property management 10% $215 - Office/Travel/Legal 4% $84 - Mortgage 26% $552 - Monthly Cash Flow - $316 per month or $3,792 per year so Cash on Cash = 17%I think this looks like it is a deal worth doing and I also believe I can bump the total rent up by $50 each tenant which I think make it even better.

But the trick is they claim very little income or never file taxes at all .

., 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%?

@Luis Cerwin as others have stated, Nov - Jan is the worst time of year to have a vacancy.Majority of tenants live paycheck-to-paycheck, so all their income goes to Holiday spending starting with Halloween, then Thanksgiving, then xmas, then NYE.January is also historically the worst month for rent payments due to Holiday Hangover Spending.

How could I best secure financing for the renos to get each unit up and income producing?

You have used home equity lines of credit to purchase investment rentals and want to know the best way to pay down the HELOCs.Between the two properties you bought, after expenses, you have $250 a month positive cashflow to use.What I like to do is pay down some principal every month with my positive cashflow.I use my extra active income from real estate commissions helping other investors to pay down the principal even more which just frees up that credit for me to use again.I know I can refinance the HELOC debt before it changes to principal and interest as it is just interest only payments as yours are.One difference is the cashflow, I have greater positive cashflow and could make the principal and interest payment in the future with the extra cashflow I already enjoy.I always get HELOCs on my income properties as well after purchasing them to pull out as much of my downpayment as possible.

Multiple people had some bad things to say about the area, but when I moved and realized that it was a low income area with a lot of homeowners, I was motivated to improve the property to match the effort my neighbors have put in. 

If they qualify as tenants, you might need to honor tenant rights or negotiate a settlement to vacate.Market Potential: A two-family home and a single-family unit could be a great income-generating property post-rehab or resolution.