Location. 25 minutes to beach, 40 minutes to Florence, 15 minutes to Pisa, 60 miles to snow skiing.  10 minutes to Home Depot style store, etc.  

I've lived here my whole life and have really seen a dramatic change in this amazing city. 

Hey Account Closed - I highly suggest  using a renovation loan and house hacking a multi-family if that is possible with your current life circumstances.The 203k and homestyle renovation loans are just amazing products and drastically help you reduce your risk, in my opinion, because you are able to leverage the cost of the entire renovation with such a low down payment loan.We work with a lot of clients who use these products in Chicago, and no matter what, in the long term, they gain great equity.If you aren't able to house hack - the process is essentially the same, but just with more money down with hard money or conventional construction loan.

I'm not sure what you've heard or are expecting, but as with anything in life you generally get out of it what you put into it. 

If your problems were really caused by an unexpected ac failure (can’t believe your realtor didn’t get seller to throw in a home warranty.) and not lifestyle.

My mom is nearing the end of her life and has left me and my two brothers her condo in Hawaii.

Gave up for a couple months as I have been swamped with life. 

Statistically, I would bet that many of these properties could be at risk from a similar event before the reconstruction could even be completed.What is the new premium on a $5-10-20M insurance policy and how could it ever be recuperated during the life of the policy or length of the average 30 year loan? 

Needs all new cabintry, windows, doors, roof (has some life left), fixtures, fencing, some electrical and plumbing changes, and some framing/drywall due to termite damaged sill plate in areas.

OK, good luck with that if you have easily accessible assets like a home you don't live in.Meanwhile, what are the odds a term life insurance policy pays out?