@Logan LarochelleUltimately, everything you report on the return can be questioned by the IRS...will they...Your role is to report an accurate return based on the tax laws provided to us.If the IRS questions anything you should say you are excluding the gain via section 121.Show them the closing documents on the day you purchased the home and the closing documents when you sold the home.Then to show that you lived in the home for 2 years - show them the receipts of utilities that are in your name.Likely they won't audit you - but in the chance that they do - you should at least have the documentation.

If you're not clear on your role in the process and what your process is you will experience a lot of setbacks. 

You may be better off finding a partner to go in on this one (split building, negotiate roles & responsibilities due to financial qualification assistance needed to obtain property).  

So, I urge you to be ready to be flexible and pivot: meaning if you find a good deal and you cash flow $200/door, don't be discouraged or assume its a terrible deal. 

That said, based on the info provided, and being in So Cal myself, I would replace them all, reframe the Arch out to rectangle keeping the largest opening for light and view purposes, and get a bid on several window manufacturers for best pricing.Design and quality of your finishes will play a big role in your exit value.

Have finally settled into my new role and am looking to step back in.

Have been in mortgage lending for about a year now and looking to pivot to an individual/smaller company so I can see how deals are done (wholesale, flips, rentals, anything).

If it's a big value add, precision on finishes is not required and you learn and pivot as you go. 

If being a REI is more trivia about you and doesn't relate to the role itself, then I would leave it off.

We have two family members that we want to partner with, however we are unsure how to establish roles within our group.