His family made their money with W2s and the stock market.

We do want to settle in a little bit here while continuing to do our homework, but hope to get into something in the next 6-12 months.With the way interest rates are looking now and what little I see on public listings, I think a smaller multi-family that needs a little rehab would be the best bet. 

Quote from @Makani Donaldson: Even when the market was great for investors (2012 - 2020), most investors would say good cash flow was $200+ per unit, per month.

Can we seller-finance his house with a promissory note of some kind even though he still has a mortgage?

Even high density local population areas I would not want since most don’t make that much money.  

Even at $110k I think you are pushing it as if you were to get a loan for $150k say your holding costs for that loan and closing costs could be $20k+, then you have selling costs of say 8% which is another $16k.

The time value of money still favors acceleration, but only if you have a clear path to eventually utilizing these losses.Don't let your tax savings get trapped in passive activity loss limbo.

I manage a coinvesting club where we invest once a month in apartments, trailer parks, vacation properties, land and recently we even invested in an industriall company.

House hacking locally is typically going to be the least risky way to get started, even if it is more expensive of a property.

I’ve been seeing some real opportunities coming to the Multi Family Market, but the best deals seem to be moving quietly, before they even hit the market.Curious—what’s your approach this time around?