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 :)

I am wondering how the math works when comparing one 2 to 3 bedroom house with one 6-bedroom house since I am wondering if a 6-bedroom house has less bookings and higher costs for cleaning, insurance and maintenance.

Currently, the rent from them is 14,000 -$15,000 a month.My question is, how much less would expect to receive if selling them as a group compared to individually.

I can run rent comparables for you, but yes that sounds right for virginia beach depending on the condition.