You'll want to print and save the SS-4 Letter that you'll have the chance to download at the end of that process.

But, as my wife and I have done this over the past 5 years, we have found it moves less and less each time, and that we are essentially living the life we envisioned 5 years ago when we started this process. 

At it's basic level:Assumption: Asking the bank to turn the loan over to you and going through the normal underwriting process, credit, income, DTI ratio etc SubTo: Taking over the loan without telling the bank, no underwriting, no credit check, no income verificationBoth have risks, but it's not my intent to be detailed in this post.

Is it worth it to go through the proper process with the city and run the risk of a huge expense to make this a 3rd unit? 

And using the process buy a new property or properties that you also intend to hold for investment use.The issue for you might be that you purchased this property with the primary intent of selling. 

Key points include:Security Deposits: In Indiana, there’s no legal cap on security deposits, but you must return the deposit (minus any valid deductions) within 45 days of the tenant vacating the property.Evictions: Follow the formal process carefully.

This started my thought process that maybe I should sell. 

In that case, would the renting process be a bridge to help you retain the home for future personal use? 

However, I had to subordinate the sellers note to 2nd position (hint: set up that language in advance to streamline the process, if that's the direction you're going to go).Since the ARV was high enough, and the potential income would support the mortgage and expenses, it all worked out. 

I realize I am not cut out for the entire REI process of consistently finding multiple properties for particular exit strategies.