We could have therefore remained in compliance with the rules to only have one FHA loan at a time but not needed to wait so long to refinance after the first year expired because the other person would have been eligible to open a second one. 

The next best time is when you decided you want/need to sell it for business reasons: current market is favorable, you have a better investment opportunity, you have an offer you can't refuse, and so on.The worst time to sell is when you were waiting to sell due to tax considerations, and now you can't sell anymore.

If you can visit, that's great, even if it's just to get a general lay-of-the land.Understand what your goals are and what property classes you're targeting (A/B/C neighborhoods).

But wait - cost segregation!

So I would educate them on the fact that they were given a gift for many years, and now that you have finally chosen to raise rents to market (so that you can make the profit that you deserve) they will have to wait for a year so that you can put aside some of your new (and well deserved) rent increase to pay for their nrew floor.

Buy & hold then wait 10 years.

I’m ok planting some trees in todays environment and waiting a decade for it to produce.

In the end, if you have a good relationship with the companies, don't wait to ask for a call with the stakeholders. 

Bigger Pockets has been giving me knowledge and encouragement to take actionable steps and I can not wait to post my first deal.If you're reading this post, thank you for taking the time to do so.

Should I wait for the tax filing then?