He explains enough that its compelling, creating flexible pricing strategy to drive your calendar to maximum revenue and occupancy BOTH at the same time (which some say is impossible, but it is possible) I know of Rob too but yes compared to Sean he is a beginner.

Since you'll be living in one of the units, you can qualify for owner-occupied loans, which often have lower down payment requirements and interest rates compared to traditional investment loans​

I really want to understand how those rates are comparing today against 30yr fixed.

I'm also charging less than Rentometer suggests I should.There are a few equally nice units a few blocks away that charge comparable rent.

...if the vacancies are frequent or extended, it can be a big expense, so I analyze this thoroughly.As for house-hacking specific costs, there are things like furniture/appliances/decor for the common areas of the house, costs of screening applicants (like background checks), cost to advertise, the time and effort required to manage a house hack, etc.  ...although these expenses are worth consideration, they tend to be much smaller and almost inconsequential compared to the big capex expenses that can come with buying the wrong property (e.g.; you might spend a couple hundred bucks on tenant screening, but a new roof might cost $20k+).Back when I was house hacking regularly, one of the most significant "costs" was the cost of my time and effort to acquire tenants (which includes all the time and effort of posting ads, responding to inquiries, answering questions, doing viewings, screening applicants, managing tenants once they were in-place, etc.).

To assess what type of upgrades to do and which will return for you - do some research into what other rentals in the area are renting for and scope of renovations they have - i.e. if the comparable rentals all have painted the 1970 cabinets - then you can do similar and not drop $40k+ on  full gut/ remodel.

When you look at the comps, try to compare it against the ones that are from the same neighborhood.

Which is why it helps to look at the surrounding properties that it pulls the comps from to see what you are comparing. 

Compare your cost of ownership with the cost to rent.

I agree with the others that three months is way too long and indicates something is seriously wrong with the marketing.You (or the person marketing the property) need to really study the market and look for comparable homes (location, size, amenities, quality, price, etc.).