To buy or not to buy

I am looking to buy my first multi-family. The current deal I am evaluating looks like this:

2 X 4 family units next door to each other

Asking price $289,000 each

Offer $250,000 each

Rent is currently $550/month resulting in a conservative cash flow of NEGATIVE $4,500/month

Units are out of date but in good shape. I believe that updates of $10,000/unit would result in rent of $750/month minimum (850-900 would not be out of the question).

If I conservatively estimate 100k in updates and 750 rent, cash flow becomes $8,300 with 1.28 DSCR. Needless to say, if higher rents are possible, the numbers get much better.

I am attracted by the property as it is in a B+ area where I would be very comfortable learning, sending my wife to show an apartment etc.. On the downside, I am nervous to overpay based on current financials, but the upside appears to be reasonably easy to achieve.

Thanks for your thoughts!!