Hoping to go down one of two paths:1- Buy a condo or small single family home and build equity and create value with my maintenance/construction background.2- Find a cash provider to do this on a larger scale with a 3-5 unit building. 

Once you take over a property as an owner occupant, if it is a single family or condo you can live in it for 1 year and that automatically exempts your unit from rent control.

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I don't think you are going to be able to get insurance for two separate living units in a single-family when they are both illegal and likely do not have the correct egress windows (basement) for fire safety which could subject you to huge liability if something happens to either party.

I currently have a single family rental here in Indy (since 2019) and looking to network and learn more on multi-family commercial investing before making the leap. 

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Hello Bigger pockets just dropped the blog link attached with current hedge funds buying single family homes .

If you are single or married with a small child, buying a duplex or 4plex should work well.  

Is it possible to re-finance these separate properties as a group in a single loan?

We provide new construction rentals and PM (single family, duplexes and Quads) for investors.