Compare this to your insurance deductible, which can be high near the coast and, as you mentioned, can be higher during a named storm.One wind claim during a catastrophic event should not cause your insurance premiums to go up, but if you have had multiple claims in the past 5 years, the frequency of your claims could cause an increase.The reason I do not advise you to call the insurance company first is that it will be entered as a claim on your policy, even if you ultimately do not receive any money from the company.I hope this helps. 

Way to go, Frank. 

It would not make sense to go through the hassle of getting a mortgage on a property (if it even qualifies) just to turn around and try to refi it a few months later.

I looked at what air bnb's seem to go for there, and with a 20 out of 30 night per month occupancy, it would not only pay for itself, but cash flow nicely.I'm not a new investor at all, but completely new to this type of model. 

He is actually really looking forward to going to the new place. 

We would be looking to go down during unoccupied times to stay for extended weekends and during summer for some breaks when unit would not be occupied.  

A 203K may be a good loan to go with, but I'd keep an open mind.

I don’t have time to go door to door cold calling to find off market homes so haven’t gone that route.

We definitely have a well written out LLC with a good operating agreement however because the mortgage note itself is in the name of one of the partners, I’m unclear as to whether he specifically is at risk if something were to go wrong at the property.

That PM has got to go.