He is thinking about adding a 2bed/2bath to the backyard or next to the house.My mom is 60 and my dad is 59.

The information contained in this post is not to be relied upon.

The only change is adding the new tenant.

I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.  

Which makes my answer, as opposed to yours, applicable.Especially since I qualified mine by adding "...unless she adds more real estate work"Your argument reminds my of an old joke:- Doctor, will I be able to play violin after this surgery?

They save me some time and give me a little added protection but that's about it.

In the past 10 years, Ocala has greatly improved the employment base, adding tons of logistics and distribution jobs on top of the medical, service and equestrian jobs that we have always had. 

After acquisition, we furnished it, added a couple decks for a hot tub and solo stove fire pit, as well as a ton of string lights and were off to the races!

I have it narrowed down to two agents, one has more general experience in the area and are part of a large organization.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor."