In regards to what you said about goals, how much of an impact does that have on the timing of refinancing a loan?

You need to evaluate how the additional interest expense will impact your cashflow. 

How much will this impact asking price for rent if we leave as is vs renovate?

Flat roofs, old roof age, old electrical, cast iron plumbing and non impact openings will mean much higher premiums. 

In your situation, depending on what you want to do next, a 1031 Exchange could make a huge impact.

*However, when I made it clear to mortgage brokers that I did not want the DSCR lender nor the servicer to report to the credit burueas or impact my DTI, they said that they could accommodate that as long as the loan docs and the title are in the name of the LLC (borrower = LLC, not me personally).

Some people (hosts) seem to manage everything remotely just fine but after doing this locally for several years I don't see how that's possible as crazy things tend to come up during guests visits that have to be dealt with quickly or they can have a serious impact on the critically needed 5-Star guest review. 

Factors like zoning regulations, property size, and potential impact on your primary residence need to be considered.The ADU process can take time.

Initially, selling agent commissions may be lower because of this ruling, but after they take on the work of the buyer agent for some time, they may set their commissions higher, or set service levels that will impact the efficiency/effectiveness of selling a home. 

what I'm not sure of yet is how the bill will impact the double close strategy if you're not licensed. in any case if there are any investors (experienced) who are interested in being on my buyers list let me know!