As a wholesaler I would say that this probably wont benefit you much unless you can close on the deal and resell it.

HOA and back property taxes will be paid prior to or at closing when they resell it.....no need for a delay to resell it. 

First option: Close on your properties (whether or not you can find a buyer) and resell them. 

And its the same thing in our state with rehabbing houses to resell hardly anyone knows that you need a developers license.

I think you just need to buy your inventory then resell it.. or if you simply want to make middle man fee's get a license and go forth in that pursuit.

From what I see and I guess we wholesale but we close first then resell.. but for those that are basically acting like brokers..

- How should my strategy differ if I want to resell these units in 2-3 years?

The better location of being closer to downtown would likely reduce vacancies/have way more resell value but then you would need more roommates, does anyone have experience house hacking multiple properties and seeing what worked best? 

I concur re selling vacant.

The investor was supposed to by the property via "subject to" and resell it to him in a year when he was in a better position.