@Will Glaeser  I think it would be easiest to build experience and a track record of success in Area A and then transfer the experience and track to Area B to continue to grow your business. 

Preferably it would be the 4plex so that as cashflow is generated you can continue to work on the 5plex.

I continuously see new flip properties hit the market and when I check the tax records, they are purchased from sheriff sale.

So in that sense you've got plenty of time - both to set up the 1031 and to continue your due diligence for your replacement properties.And although it may feel daunting you've done a fantastic job of distilling down the questions. 

I currently own one property that I rent out to some roommates (almost like salvage renting) so that has been going well and have thought about buying another property but working the job I have now feels like I don’t have the time to really dive deep into real estate and continue to grow and learn about the industry and find the best deals.

For some reasons many brokerages dont understand they actually have to make money to continue to operate.

Like continuous leads and communication that I don' have to do.  2018 is about removing myself from being "in" my business and working "on" the business. 

I don’t have any plans in the near future for it, but I’ve been continuing to search for more deals to build off of what I’ve done so far.

The other CPA said that I should continue with the original schedule, but only claim depreciation for the years it's rented.

If you are going to continue renting to a dormitory-type situation, it might be worth your while to pay someone $50 to go in your property once a month and make sure the tenants are keeping the place hygienically acceptable.