In addition, education can only teach you so much - what type of experience-based learning do you receive when joining these teams? 

Additionally, his credit is not the best, and he has limited funds for a down payment.Any potential options or solutions that may be available?

The unobstructed water views for both front STR units can be challenging to determine additional value compared to other 3-unit properties without views.

In addition, due to them being eligible for conventional non-commercial financing they typically have lower cap rate than 5 units and more.  

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

Principal balance currently at 314kProperty Details: It's essentially a "2-in-1" property, with the main unit rented out for $1,900/month and an attached ADU bringing in an additional $1,200/month.

Additionally, we are approved with the Better Business Bureau (BBB).

Electric: is the easiest to split, but may require holes cut in walls to separate the units.Gas: gas lines aren't as flexible as wires, but it can usually be done affordably.Water: most cities will NOT install additional water meters on a property.

Additionally the renovation costs are going to be higher as you have to re-draw the floor plans a bit (and add in sprinklers bc its a four fam) but the great news is that you would be able to finish the attic to create larger units on the second floor and get more rents.

Not sure the cost of this for you but I feel with hot tub and fireplace you already have a lot of warming options and not get much additional revenue.