My initial reaction from my walk through above would be that the holding period in the Real Estate doesn't begin until you have the rights and benefits associated with the real estate - so the earliest at the end of the redemption period, but really beginning once you take possession and can start doing stuff with the property.Some further digging I found some examples of it, but if you were a paying client I would be spending more time to see if there were any subsequent changes to this rule - at the very least Bloomberg isn't calling it out on me ;) . 

We also considered converting the garage into a 3rd bedroom to add value through live-able square footage but aren't sure how far we should go with it before we start looking into a cash out Refinance.

The deal exemplifies our ability to deliver outstanding results through strategic investments.

The rental market is still extremely hot and prices are high with inventory low, but I have still been managing to cash flow on the new purchases.     

And I’m planning to get business credit through my LLC I’m setting up.

The deal exemplifies our ability to deliver outstanding results through strategic investments.

I am aware of the Sewage issue and i am aware that in this high interest regime it won't be a cash flow property.

Most are actually pretty helpful if you reach out and ask questions in advance vs being hostile when they make you jump through hoops completing applications and preparing for the P&Z hearing.

Assuming it's Section 8 approved, why would it not be a good idea to slap a Section 8 tenant in there and collect positive cash flow?

@Andy I chose Buildium when going through the process.