I am actively looking for another 10-20 unit building that is within my self imposed limit of one hour drive away.

The only thing I would watch out for are the rules and regulations imposed by the city of Seattle for rentals within the city limits. 

Additionally, this is not just limited to CT.

One thing I have read and heard here at bigger pockets is the power of networking in your local area.

There is a $2500 limit ...you’re Referring to the 2016 de minimis safe harbor election taxpayers can take for the improvement of existing property that otherwise must be depreciated?

You're most likely limited to 75% LTV on a cash out refi, per Fannie Mae guidelines. 

Main job is working at a power plant, but am very passionate about giving real estate a go.

@Samantha Soto @Casey J Burkhead is correct.  1 policy listing 2 buildings is the correct way to set it up.If there is a limit to the # of rentals, then you are working with Personal insurance policies. 

Because of this limitation, the properties with ADUs in my area of investment are being comped at a discount compared to duplexes which seems reasonable because a duplex can be purchased by a house hacker or an off site RE investor but the ADU can only be purchased by a house hacker/home owner.Check this for your area. 

One last point: It is important to ask if they have any limitation on the amount of profit spread between the A-B and B-C transaction.