Quote from @Amit Chugh: @Tim Delaney - I was referring that one of the properties is listed as Section 8 Property, why one would list that in title, does it make any different or benefit for buyer or seller mentioning section 8 in title?

HUD loans will take drastically longer (I've never used one personally), but there can be benefits to using these loans if you're a long-term owner.The interest rates in your Key Considerations seem very low for agency loans and they're definitely low for bridge loans. 

Both @Nathan Gesner and @Lauren Stark have provided valuable insights on this.One potential path for you is to join an established team to gain experience.

Forming an LLC for your rental property can offer liability protection, but no real tax benefit.

I would imagine the LLC will have its own EIN, but we will still report the gain/loss as pass-through income on our joint tax return.

My son is working on his first SubTo real estate deal in Crawfordville, Florida, and I'm hoping to find someone in this community who can offer him some guidance and support.He's eager to learn and navigate this process successfully, but could really benefit from the expertise of someone with experience in SubTo transactions.

It will familiarize you with the basic terminology and benefits.

How much weight do you give to the cash flow benefit of cheap debt when the property is priced above market?

But have you gained anything? 

Oftentimes non-real estate specific CPAs aren't super familiar with all of the benefits of a study.