For example I see a couple of houses in my hometown Dyersburg, Tn that are up for sale which to me signals some kind of motivation to sell.

What kind of repairs does it need? 

Make sure they assess risk like you do, make sure they have some experience themselves, and what kind of returns they actually get.

Still, with the cash in hand, do you have an idea of what kind of cash flow you could get from a replacement investment? 

I've obviously seen all kinds of wholesaling contracts around the internet (Purchase & Sale, Assignment, etc.) as well as several JV agreements, but I have no idea what kind of agreement it would take to put that kind of arrangement (someone inspects the property for X% of the profit of the potential deal) into writing.

The past year it's all been going pretty smooth but kind of feel like I wont get lucky twice with another easy going rental lol. 

If I decided to invest in commercial multi family, what kind of investment I should be looking for 20-25 Units.

Decide which kind of investor you want to be (SFR, Commercial, Land, Tax Liens, Passive, HML, Multi-Family, Notes, Fix & Flip, Buy & Hold, “Subject To”, apartments, duplexes, assisted living, REOs, Foreclosures, Short Sales), etc.

I'd kind of like to go with a conventional loan, because I want the lowest rate possible.

I'd kind of like to go with a conventional loan, because I want the lowest rate possible.