Are there pros and cons beyond just the level of security between having a contractor list your LLC as a certificate holder as compared to being additionally insured?

It can be useful to know and to compare assets but it's not the highest on my list of something I look at as a cutoff number.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

His SMF downside compared to my SFR in Tonka Bay (which isn’t effected but if it was.) 

If the assessed value is higher than market value, there is usually a process to contest by showing comparable properties that sold for less recently.

Compare as many lenders as you can.

The City used google satellite images to go as far back as 15 or 20 years to "prove" that all those trees were "missing" compared to earlier pictures.  

But the comparable rents in the area are around 1800 to 2300.

In case you are eligible for the Solo 401k, here are some of the benefits it would offer compared to a self-directed IRA:Solo 401k contributions limits are roughly ten times higher than IRA limitsThere is no custodial requirement for the 401kYou don't need the additional expense and administration of an LLC to have checkbook controlThere is a built in-Roth component whereas IRAs are either traditional or Roth, not bothA spouse can also participate in the same Solo 401k planThe Solo 401k has additional tax benefits over an IRA when investing into real estate using leverageThe penalties for prohibited transactions are less severe, though it's best not to utilize this benefit :)

He’s very handy, a chemical engineer by trade, and loves numbers.