So it does appear to be possible to get an FHA 203k loan for a 5-unit & convert to a 4-unit.When possible, aim for the Limited (aka Streamline) 203k loan, as it's less complex, not required to get an FHA consultant, etc.Of course, this is based of the two following important assumptions:1)  zoning allows for this2)  and obviously I owner occupy for at least 12 months3)  the total purchase price + renovations are within the FHA loan limits specific to my areaWhat I'm confused about is the timeline or chronological order of the process? 

What about if you set up a maintenance company that maintains all of the properties, then you have a real estate attorney prepare all of the lease agreements.

While I think neighborhood farming is a good idea, I'd say instead of doing it geographically, think about who is most likely to move in your community. 

Sales have plunged to 1995 levels according to one stat sheet I saw. 

@Cheryl WellmanHi Cheryl, welcome to BP!

-"analysis paralysis" is mostly a made up nonsense phrase intended to get people to go ahead and buy real estate even if they aren't ready to do so. 

LLC is most flexible entity.  

It might make the most sense to just sell your primary residence and use it as 40% to 50% down payment on your future home. 

I use Proper insurance, unwritten by Lloyds of London, for my STR - covers the extra issues you would expect from an STR like vandalism, alcohol liabilities, business interruption up $10k, hot-tub cooties etc.

Most 1099s are available online now, and if not, you can always scan them to an electronic format.