After debating with myself, i figured since I am a younger male with no family the best route would be for me to house hack a Multi-family, and rent out the other sides.

Im debating on getting a HELOC to put a down payment for the investment home or getting a personal loan. 

Peter Gray Im also from Sheboygan and have been debating about investing here or in Milwaukee.

Or lets start a political debate on deed and use restrictions as to whether or not a property can be used as a residence - Trump & Mar-a-Lago link below https://www.washingtonpost.com...

Anyway, I was debating whether or not to go after my real estate license to add to my income .

You might as well get your advice from a palm reader.There is nothing to debate here, because only the future will reveal if 2017 was a good time to invest. 

I would not be surprised to see security deposits disappear completely in ten years or so.some of my clients in MS  years ago got away from this and simply charged a 500 or 1000 dollar non refundable move in fee.so at the end of the lease there was not this big debate about the security deposit.. tenant new they had nothing coming back and landlord mitigated whatever turn over costs with the on refundable move in fee.. 

I'm not going to go into the debate about whether the US or Thailand/Asia is "better".

At the Santa Cruz BP investor meetup last week I ended up in a debate with @Troy Fisher regarding cashflow Vs equity investing.

No need to debate, it’s not like you have a choice here.