If this is "light work" and you have great insurance and a great PUP (Umbrella) Policy, then the risk might be considered low.

Unless you are holding a huge number of properties or there is something unusual about your specific situation I question the need for even a single LLC.Most people can REALLY accomplish what they think they are accomplishing with an LLC simply by making sure they have a good umbrella insurance policy in place.

Even with umbrella policies, oftentimes they will still require a "deductible" of sorts before they pick up any additonal coverages that the primary policy doesn't cover.

As far as insurance goes, get a Individual or Umbrella policy?

I mentioned those two specifically because I currently have accounts with them and thought may be it'll be easier and more flexible if the solo-401k is under the same umbrella.#2 - I assume one has to be very careful how much to roll over.

I have pretty high liability coverage...i think $500,000 for each property.On top of that, I have a $1,000,000 umbrella policy that covers me in case anything happens and the other insurance runs out of money.  

I would just leave everything in your own name and get a liability umbrella policy that covers you for the 1 property.  

I'm going the umbrella route for now. 

Thank you for the advice everyone.I am getting an umbrella policy for primary asset protection & set up a Wyoming LLC to manage the finances.

Just get good insurance, 1-2M umbrella.