During that two year period I had an opportunity to make a few updates to the property which gave me invaluable experience working with contractors 2.

Or is there a period of time required between using the capital gains exclusion?

Total of 11 single pane windows and wanting to get energy efficient replacements .

I just started a new position that I am loving, however, it is only contracted for a year (slight chance it will be funded for a longer period of time) and the pay is minimal. 

Or is there like a waiting period?

If your reason is "I am trying to buy 10 houses using owner occupied financing over a 10 year period as a way to work around the guidelines and acquire investment properties with 5% down"  then that might raise a few red flags. 

And then have them stop in periodically if you want them to check up on the property.

As long as he's allowing the home inspection period and the first purchase from him wasn't full of hidden problems, then it might be a win-win for both of you.  

The period that the property was being rehabbed and fixed up initially does not qualify as rental period.

And isn't inspecting the unit periodically actually their job that they are already being paid to do?