During the Lula setup process, select "I will choose which maintenance requests will be sent to Lula" instead of opting for all requests to be sent automatically.

So first, I'll answer your question then I'll tell you what I would do if that matters or you care.1) I don't see a need to choose one or the other. 

If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

The equity market is a fine comparison, but the reality is if you think every 5 years you're net return will be 90%(not sure if this is pre or post tax) then you can choose that route but you have to mark it to that return annually which is a reach.

There are limits to this as well (when someone stays the whole time and doesn't say anything while there), but if someone chooses to leave early or right away, give them their money back before they drill you with a 1-star review.

Lead paint testing requires no supervision or follow-up inspection.

If you choose to move forward, I recommend having a backup plan in case Hawaii outright bans STR.

You can also leave out some bulk hotel toothbrush/toothpastes, make up removers, earplugs, sleeping masks, etc. if you really want to step up a "In Case You Forgot" basket.You can keep a closet with extra of things that has a lock on it and if someone is irrate because they don't have enough pods, you can at least have a back up solution for them if you choose too. 

One of the board members was there and is looking to retire, We hit it off and he opened up his 30+ property portfolio to me to choose from.

If you decide to exit real estate entirely, just make sure whatever investment path you choose aligns with your goals and risk tolerance.