Planning ahead can be challenging when two nearly identical loans get UW and conditioned in very different ways at the same lender.  

Sorry for the typo, Bigger Pockets doesn't give me a way to change or edit the title of the post.

I like Chicago Title out here in Riverside/San Bernardino.

It can be to season title, or in your case to season the value.

I setup an LLC for my purposes of renting my first home and I am wondering if I need to transfer my mortgage / title of my first home into my LLCs name instead of my wife and my personal names. (1) Is it required for me to transfer the ownership of my first home to my new LLC?

With a setup almost identical to wholesaler lists I get emailed to me daily.

That's rare.You could probably do a 2nd for the $10,000.Talk to your title company or title attorney and have them draw up the deed of trust and loan terms for the 2nd. 

We have used Title company in the past to transfer our rental properties to LLCs.

Rent Roll13. property survey14. prelim title report (your broker can help with that)I DO NOT Ask or recommend my clients ask for tax returns, credit reports, bank statements - These fall into financial privacy protections and if my buyer walks from the deal, there is too much liability & risk with having that information if were to be leaked.If a third party management company has been managing it, you'll get basic information (income/expense, rent roll & leases, maintenance records, capex (maybe if they oversaw)).Owner operated properties will have less of this information as most mom/pop operators don't keep good records, in my experience.Don't worry about all this BEFORE the offer. 

And the s corp has to take title to the replacement property in the 1031 exchange.