The property was rented and generated $160 cash flow after mortgage, taxes, insurance and property management fees were paid.

They are asking $375K but not getting it - so not quite $20k underwater from asking but they're offers so far are around $350k and lower.

On property number one, I would cash flow $750 a month after mortgage, taxes, and insurance if I also rent out the unit I live in.

Should I have one website advertising both and have business cards list that I offer buy/sell realestate services and PM services.

You payment is $2,600 plus tax and insurance.

Small multi-family properties starting at over $1M, which is pretty expensive and, resale single family (before year 2000) offer minimal cash flow (~$200-300/month).2.

As you know in many real estate deals, the money is made at the buy.Personally, I'm focused on off-market deals where we can create value.Curious—how did you frame your offer to get them to drop without hesitation?

Propose starting small, like a single-family rental or house hack, with a clear, low-risk plan to minimize concerns.Leverage your industry connections and offer to handle the initial responsibilities, demonstrating your commitment and capability.

I think she is equally responsible if she is 50 / 50 ownership per the offering and through thier own discussions on podcasts, social etc. 

@Andrae S Wiggins recommend you upgrade your BP membership to Pro to access the BP Calculators to evaluate rental purchases.Play with the numbers to figure out the purchase price that gives you your target ROI.That's the number you'll need to make an offer at, NOT what the seller is asking.Yes, you will get a lot of rejects, but whoever said investing was easy?