My goal is to create generational wealth for my family and to eventually have the financial freedom to say "yes" to travel adventures as a family. 

Selling and exploring a 1031 exchange could make sense if you can find a deal with stronger cash flow or faster equity growth, but the key is comparing your current return to what your skill and experience could generate in another investment.Here to help,Jorge

My goal is to rent it out to start generating some cash flow.I’m planning to remodel the kitchen soon, and once that’s done, I’d like to move out to make the apartment available for renters.

With 4 rentable rooms (including the basement), I expect to generate $3,600/month with full occupancy.

I mean I think about it a lot now that we are closing in on 70.. but hey 70 is the new 50 :) And different cultures handle this far differently than others.. this is why you see some new builds catering to multi generational floor plans..

The report is as good as the answers you provide to their questions.The risk is that you answer a question incorrectly which generates an incorrect report.I would have a discussion with your CPA to determine what the land basis is(required to start the cost segregation).I would also have your home inspection / appraisal on hand to answer the questions more thoroughly. 

With a 7% interest rate and high HOA fees, the key is evaluating if your skills and investments can generate higher returns elsewhere.

. - if I use my cash, the investment needs to generate > 5%.

During this time you are not generating any return from the money invested in the ADU.

The money generated could pay for both loans, and even cash flow.Italian BuraccuracyI thought the United States is slow and has poor processes set, but here is absolutely worse.