The only way to sidestep it is not to self manage, and hire a PM with his own E&O insurance, and he's responsible to get someone to cleanup the snow.

I am trying to hire a handyman to assist with some of the work, but most insurance companies are not interested.

I'm ok sacrificing some returns for hiring out anything that takes longer than about 15 minutes, and at this point am pretty much assuming that I'll be using property managers.  

So, I need a contract, I assume I will do a title search, have the land surveyed, hire a lawyer (I have one through work that will do RE stuff) to deal with title transfer and filing or is that someone else?  

Hire a professional to give you a quote.

Also, if you're not skilled at rehab design (interior/exterior design), I HIGHLY recommend you hire a designer.  

If you have the funds, you could save time and hire a professional cleaning service to do a thorough and nice job for you.

Since then I have also hired a property management company in Maui to run 1 of the condos.  

You either need to proactively seek the information, or hire advisors and pay them for their expertise.

Said she is too old and doesn't want the hassle, though she recently hired a new property manager she likes.