On the surface, the deal seems appealing, but there's a catch: the asking price is $475,000, which is about 18% over the market value (based on comps and DealCheck estimates around $402,000).Details of the DealProperty: Duplex, 2,400 sq. ft., 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%?

At the end of the day its about price and terms. 

A good designer and architect are key for a successful project like this and keep in mind these aren't cheap.There's a lot more details to consider, feel free to DM me for more details.

Will you use the HELOC as a short-term bridge, or plan to hold it longer?

We don't bait and switch, we work deals based on actual details of the client's specific deal.

Sometimes the long term capital gains are palatable and it may make sense for you to pay the tax rather than force a bad deal.

Are there any resources that help explain what type of terms we should ask for?

I also allowed the fear of others to take me away from my long term goals.

I used to provide detailed answers to DMs, which are private and help only the requester.

I have three listings, 1. unit with a pool and hot tub, 2. unit with a hot tub, 3. both units together as a 12 sleeper.Gross monthly income (after booking channel fees) for the first unit over a 7 month period was $7309.Gross monthly income for both units over a 14 month period is $11,297 (after booking channel fees) As a long term rental the combined rent would be in the region of $5500.Is it possible to sell the property based on the income generated by the STR business or would the value always be based on bricks and mortar comps?