We want our kids to be able to be close to our families, so ideally, we visit Oahu a few months every year.I spoke with a few realtors and it seems like the best investment would be the condo hotel as they are legal Airbnb/STR.

Wish I could be more help. 

The broken kitchen sink needs to be replaced.

If you sell it, buyers typically prefer it to be vacant so they can pick there tenant, so I would not be worried about that.

It took a few days for me to be confirmed, so knock it out early. 

I want to (willing to) learn everything I can but I do not want to start a new career but I 100% want to be in real estate!

I specialize in this type of transaction and would be happy to have a conversation including why they may not be a fit for you. 

There used to be, but they stopped supporting it, so if you switched phones and needed to download the app again, you'd be out of luck.

My one tip would be, its not about getting wealthy quickly, but more long term.

As far as home office no longer being an IRS "red flag" I guaranty that if you put a home office deduction on a personal return on Turbo Tax it will move their audit risk needle.