Study different exit strategies, choose one based of off your goals, timeline, and risk tolerance, then find a mentor. 

You will have zero tax write offs because you are not paying income tax because it is a 401k.  

Was the house paid off or did you take over payments? 

If you're making decisions based off of fear of what others think of you... then you might be better off buying a nice multifamily property and living in one of the units. 

Sure, managing what you've got is important, but without a deal, you're just spinning your wheels.Now, when it comes to buying up properties, multi-family ones are a whole different ball game compared to single-family homes.

The industry is seemingly caught very off guard by the massive failure of NAR to communicate the potential outcomes and timeline of the agreement to its members. 

I have a few different deals but I have found an off market property that I am interested in.

We do have some student loans that would be nice to pay off and be free from.

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.

Great you have 1 good agent - now try to find more and simultaneously develop other strategies to find deals off-market.