You’ll need to find a GC on board with the extra paperwork and a seller willing to accept a longer closing time.   

Highlight the “family-friendly” perks, like extra beds, pet policies, and flexible terms.

 - a study on rent cost compared to ownership cost shows that virtually every large city market it is initially cheaper to rent than own (I believe is was cheaper to went in 97 of the largest 100 markets)Miami and Florida have extra concerns:- insurance difficulties have resulted in large increase in insurance costs.  

My opinion-- buy in the winter, underwrite with an extra long vacancy, get some seller concessions to defeat the cash flow if it's really that tight.

If you can tolerate it, go for the extra roommate.

- Rent out the extra bedrooms in your unit to roommates or for even higher rent on Furnished Finder.- Rent out the other unit as STR or MTR for max cashflow - which will require you to become an expert at those businesses.- Learn how to do your own repairs & rehabs to save money now.

Just having an extra kitchen doesn't impact insurance eligibility. 

I'm soon closing on a multi-family property that has some extra space that's begging to find a better use. 

Now your fully renovated home is getting top dollar rents, you could probably refinance too since rates are poised to go lower (lowering your monthly obligation), you could open a HELOC before you move with the extra equity and use that to fund your next deal and now you have 2 homes! 

In practice, this could mean 5 extra days that no rent is collected.