I'm ordering title searches and am trying to avoid having to pay for more title searches than needed.

I did a MLS search, and there is definitely nothing close to what you have in your neighborhood. https://www.zillow.com/homedetails/1066-28th-St-Oakland-CA-9...

I don't think it should matter if the deal is seller financed, cash, or hard money; the title search and insurance process should be the same.

I am also in search of a PM right now and interviewing few candidates

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

It is true that as much as it is tempting and desirable to focus on a hundred things at the same time, actually staying focused on a specific thing and trying to master it is a difficult skill.

I got 3 sellers leads out of 1 post and all are very different in their desires, but that is one of the themes I'm seeing. 1 seller even based his value off the Zestimate, and little does he know in the area, the zestimate is/resembles that of the ARV and NOT the current value. 

It's likely, you are being too tight on your comparables or not searching correctly.

I am looking to get into investing specifically house hacking and am searching for a small multi fam (duplex, tri, or quad) and haven't found the one yet.

Unless you are a seasoned real estate investor with professional title searching skills, I wouldn't do this.