I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment. 

Rents should be a modest $1500 per side, depending on the time of year I’m able to get it on market.

I appreciate your time!

As for not feeling like it's the right time, I would urge you to focus more on the goals than your feelings. 

Ben Franklin used similar advice to turn an enemy into a friend (although his was asking to borrow a book).There are some caveats here, you cannot be wasting time thus you need to demonstrate that you are taking action. 

Obviously been a rental for a long time, so lots of signs of neglect (but not gone so far that it was falling to ruin).

i tell them all the time to find a good W2 job you like and you plan on staying with a long time. 

Times are changing somewhat though, so maybe over time if they are not supportive now, they will be at some point in the future. 

@Argel Algura.Congrats first on your last.year and how much you have accomplished in a short time period. 

You should have posted a 3 day notice a few days after the first time they were late AND every time after that.