As a frame of reference, my property is 2300 sqft, mountain views, 2021 new construction, 4bed/4bath Since you're planning on using the property 95% as a short term rental I'd confirm there isn't a limit on how many days it can be rented versus used by your family when written that way.  

We do LTR and MTRs in Anchorage with the plan to transitioning one of the units to a STR.

I am NOT adding square footage or moving load bearing walls, just a face lift and new floor plan.

Unfortunately, things haven’t gone as planned, and now I’m looking to sell.I must admit, I’m quite inexperienced when it comes to selling real estate.

Do you plan on flipping in Chicago or are you looking out of state? 

So the summer has activities such as moutain biking and hiking and what not but its not too popular. we plan on reopening the business to summer activities.

Plan on 1031ing into it purchase price of 11m with about 3.5. down. 8% cap rate @ a 6% rate. 

Would you plan to live in one of the units and rent out the others or rent all the units?

Here is my second message:I have a couple questions for you to make sure its a good fit for you.

This is why having a SOLID plan in place is essential.401(k) - My partner utilized this for our initial round of funding.