You would have more tenants to deal with, but your risk of losing income is divided between the 3 tenants. i.e. having 1 tenant move out of a 4-plex and losing 1/3 of your income is less painful than having a tenant move out of a duplex you live in and losing all of your income while it is vacant. 

I would do Whatever is the least pain...…. financially NOW.You mentioned it is favourable to hold off as it is winter.

@Michael Joseph Allen IIWell say if you had to evict, it could be a painful process.

Because we are thinking of this as a flip, I would think that traditional mortgage would be a real pain?

It was doable, but honest it was kind of a pain. 

Usually that 1 tenant is disappointed with how their own life has turned out or mad about something inside that they can't control and they will take it out on anyone that they can - their landlord, their waitress, kids, road rage, picking fights on the internet, etc. until they can address the source of their pain they will continue. 

Let them move along if need be - despite the short term pain it may feel like it is causing!

The slightest thing goes wrong and you will be in for a long and nasty and very painful fall., not a good idea. 

It’s incomprehensible to me someone would spend 10$ per day for decades only to give themselves a painful drawn out terminal disease .ive heard it said by physicians that when you see a healthy lung compared to a smokers lung it’s shocking .

It's painful to get a STR going and optimized, especially squeezing a square peg into a round hole.