This for me is all somewhat of a thought experiment as I try to figure how to best position what we have for the future. - Economies of scale would be key, and right now that is not something I would have the time to pursue so this warning is appreciated. 

So the question really is fix it and hold, or fix it and sell, which might seem reactive when viewed in the future. 

just make sure to set your calendar accordingly so in future months you arent accidentally getting STR bookings and ruining your MTR chances

I am joining BP to connect with other potential buyers in my area and across the country

You would also want to move this to the K-1 activity on your 1040 tax return so future net rental income (profit) can be reduced by prior disallowed losses.Happy to help.

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To be that’s a question each individual investor/potential investor must answer for himself.  

Our company is looking to jump into SFR investments and want to look for properties in the OC area with value-add potential to either rehab or add an ADU/convert a detached structure to an ADU. 

My name is Kathryn, and I'm intending to start a mid-term rental unit similar to yours in the near future.

@Kyle Steiner Potentially you can alternate buying one property on you and your wife's name.