If you are planning on living there (ie in 1 unit) then you are house-hacking and this is a different calculation consideration then renting out both units and making it a true investment.

My post rate has went down considerably as of late.

Here's the other consideration. 

In any case I of course need to actually talk to my landlord, but I'm feeling better about that conversation the more points that are brought up for consideration beforehand.

It looks like most of them have been listed for 2-3 months, so you aren't unique.Another consideration is your distance from the city. 

We have trades we use on jobs and know what they will charge which is often considerably less than what Joe Homeowner would pay for the same job . . . the trades know we will be using them again and again. 

Once you are familiar properly evaluating a deal and identifying most of the potential obstacles, it becomes fairly straightforward and your profit margins go up considerably.

If the consideration is a prep for going into the red, saying it's easier to pace at a loss, say rents halve, with all-cash vs financed capitol, that still isn't true because one could simply use financed capitol and do only 2, deploying $40k and reserving $60k, and those 2 WILL out-earn the all-cash 1 AND have $60k sitting sidelines which can carry for literally years of an "in the red" event to revenues. 

It’s going to take you a considerable amount of time and effort to reach $350,000 per year.

You raise an interesting point for consideration.