If that's what you're really after I would start with the basics of what kind of bank loans either residential or commercial are available to you - not saying this is the best option, but it's a good place to start.

I've been an investor for 18 years but transitioned to commercial 8 years ago and the deal flow side of things is way different than 1-4 family residential.

How do I find a commercial multifamily loan that is willing to lend less than $1M?

What value is expected or provided by an agent who specializes in multi-family residential, not commercial. 1-4 units.

In fact, I've managed hundreds of homes, thousands of renters, and I've never run across one.

Commercial financing is 100% different (and easier lol)! 

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

The analysis also reports that new multifamily development will “remain near the average recorded over the past five years”.Integra Realty Resources’ 2017 Commercial Real Estate Trends Report ranks Pittsburgh #2 on its Top Markets by Multifamily Transaction Volume Based on YoY Change.Pittsburgh’s rental vacancy rate has declined by 25% over the last five years.Pittsburgh is booming with developments (see reference #6), “there is no better place to be a developer right now than in Pittsburgh.

Quote from @Sumi Devi: One of my clients is buying commercial real estate property with tenants that have 5 year lease.

I've been managing for 15 years and have helped a couple owners change/expand their portfolio.