Does anyone have a recommendation for a side hustle? I’m trying to make additional money to speed up purchasing an investment property

Seeing how little of principal is paid off in the beginning of the loan cycle, my urge so far has been to throw what I have as extra payments chipping away at that mountain, but I’ve been also thinking lately if that’s a wise practice.

Saint Charles is good, but usually cost more. 

Its hard to put all of the advice into 1 post but people usually will be happy to share with you 1:1 (including me!)

Our home and the extra lot are listed on the deed and under one mortgage.

Commissions can generally be a part of seller concessions but there are limits to the amount of contribution, particularly for investment properties (usually 2% of the sales price.) 

They are usually really responsive. 

Quote from @Clint Monroe: Trust those instincts – they're usually spot on.

Also, assume a regular job so I do not need extra income.

It also can get challenging to set a price now to possibly buy in the future that the owner and you will feel is fair (with markets still appreciating at a healthy pace).You can also keep your eyes open for a seller willing and able to do a land contract with you (but there usually would want much more money down and likely want a full pay off in a few years, but can see what you can negotiate on terms).I agree nothing illegal about options/option fees in WI to my knowledge, but generally seem much less frequently used in single residential transactions than commercial transactions where due diligence and closing timelines may be very drawn out.