Quote from @Ian Halter: The most competitive quote coming from a surplus lines insurer is surprising, it's worth reading your Declaration Page in fine print for that offer.

My parents own a house in an HOA in Sarasota FL, it was very mildly hit by Hurricane Ian, we've had a few contractors come out and look at the roof, one said we need a new roof, another said that the tiles are not up to 2005 code since it was built in 2004. 

@Ian LoonceIf it is a part of your lease, evict them.

Values have bounced back making this the most expensive MA multi-family real estate market of all time.Big thank you to Ian Hogan who is a great investor focused agent on my team, and investor in the Worcester MA market, who pulled this data together for us.

Ian,First, the Homeowners Policy form is normally for Owner Occupied Dwellings. 

Ian - you are on the journey which is great!

Ian Smith again walked the property for me and handled many of the on-the-ground things I needed.

@Joe Scaparra I an flattered but I saved up money ever since I was young and I bought a house to invest when I was 18, I would have done it earlier if I could.

@Ian Kisbert on every BRRRR property I have ever worked with there was not time enough to get contractor bids.  

I would have to agree with @Ian I Leinwand and say that it all depends on your goals.