Are you investing strictly for tax purposes?

For the purposes of property tax, they change formulas starting 4+ units to commercial models. 

Create a simple spreadsheet or written list to compare the features of each and identify the ones that align with your requirements.

What if by the time I post there is almost nothing on the market in a comparable location of a comparable quality?

@Jessica Heller- contact  several  lenders on the  same  day - provide them  with the  same criteria -  get  some  quotes and ask the  questions you have  ...compare the date and the feedback received and then make a  decison on  starting the pre approval process 

Its always been my understanding that renting in the winter months can be challenging compared to spring/summer.

I made the point to the Buyer that this is how it was purposed. 

I wrote the above for informational purposes.

You state that everything is equal but are concerned that not everything is equal...It's very possible to see a price spread like that even with comparable coverage but it's also vitally important you work with someone that has your back to make sure you understand your coverage before you'd have to use it.  

The funds would be better purposed on more turnkey real estate, but good luck.