I figured it’s about time to introduce myself.I am located south of Chicago and I have started to get my feet wet in real estate investing.

Wet basements can be very expensive to fix.

With its close proximity to the Lake, is flooding or wet basements an issue in Lakewood? 

Maybe look into wholesaling a few properties just to get your feet wet and earn some cash for your first flip or hold. 

I am currently looking into real estate investing and i keep hearing that getting your real estate licence is a good start for you. It that true or would i be better off going another route?

I'm thinking one vacation rental has to be as much work if not more than a 3 unit long term rental.I'd like to get my feet wet with commercial financing and working with a small bank and several tenants and all that jazz.

Since I'm a newbie I'm stuck between taking action and getting my feet wet and gaining experience vs being patient and finding a really good deal (which I know is difficult in today's market) 

So excited to get my feet wet in the game and hit my goals.

Is there caulking with no breaks on toilets and other wet areas?

Here is a lucrative option to consider, which is similar to what @Michael Kovac suggested: Get the permit and add the square footage including the additional bedrooms, bathroom, wet bar, etc.