You'll save plenty of money, you will also learn how to problem solve complaints and learn hospitality (because an STR is a hospitality business really).

The main issue is that to do the ADU you have to spend so much bringing other items up to code like electrical, plumbing, lighting (windows) and egress.

If a storm happens immediately after you replace the roof, the actual cash value is the same as replacement cost, so you've lost nothing.The only thing you would have to worry about are items you did not intend to repair

I’m asking because I plan to eventually scale and get into multifamily syndication, and I know learning to raise capital will be a crucial skill.Scaling with Private Lenders: Once I’ve done a few flips, I’m thinking of finding a group of private lenders to help me scale the business.

Wind is one of the subtle items that Insurance companies are starting to exclude. 

The complaint has a list of items they are suing for.

After adding those four items back in, it brings the complex to making around $6,500.

. #1 alone would typically cost you $4000-$4500Ask for a itemized list of what things would cost + his laborThis would help see where your $$ is going 

There's other items such as this where it may be helpful to talk to a CPA/EA for a little tax planning, especially since you'll likely get caught up in the passive activity loss limitations if taking bonus on a single rental property as I often see.It's also useful to mention that even if you do the cost seg study (I'm assuming you're doing one to be talking about this), you'll still benefit from accelerated depreciation in the form of shorter useful lives on the assets where you received bonus from.

Mine may be different though because I am still responsible for HVAC and many other large items on the property.