a plan to refinance our current mortgage as well as get a HELOC.

We fell in love with the island as a family and know it pretty well now.

@Jonathan WildyTechnically it is absolutely doable to have 1 app for Short Term, Medium and Long Term properties in one platform.

It's more private, you don't need a do not disturb note on your door handle for someone not to bother you are 7:43 am on a Sunday.If you want to do well in STR now it's all about the amenities and experience.

Can someone recommend a CPA who specializes in real estate investing as well as a real estate attorney?

Should I hire a contractor to add an additional meter that separates the ADU from the main house or charged another fixed amount for the main house as well.

@Jose Guillu if it's too good to be true...well, you know the rest.  

We don't do well with armchair quarterbacks.

I totally value and want a property manager to take the day-to-day management off my hands, but on issues with tenant damage and I would like to be kept up to date on matters, as well as have copies of all notices provided to the tenants for my own record keeping.

I highly recommend staying well-informed about tenant/owner laws.