Check with your lender what your new payment would be on the existing and what that would allow you to afford on your next purchase.You can still do an owner-occupied loan up to 4 units but if you're using your FHA/VA loan you'll have to go conventional 5-10% down. 

Another benefit of a Heloc is that you don't touch your current mortgage on your primary and  get to keep your current rate.

If I already own an Airbnb property (my primary residence) and plan to purchase a new house for rental purposes, what would be the recommended approach for transitioning the existing property into an LLC?

Also, you will assume the Basis in any real estate holdings which could have future capital gains implications.Pros.This is a great way to take over an existing loan subject to that would be really hard for the lender to claim due on sale default.

Wondering  if I should reach out to local credit unions or maybe a mortgage broker?

HOA is crazy at $1000 per month and mortgage is $5200 without HOA.

This is so that the lender may demand full repayment if a property with a mortgage is transferred into an LLC and a due-on-sale provision is triggered.Before putting the property into an LLC, make sure to check with your mortgage lender.

It can actually be riskier (investment wise) as you are not getting a traditional check every month, but added responsibility that you will hold onto the lump sum throughout the 3 month tenancy to accommodate for repairs, mortgage payments etc... 

☕General Question; If such a sophisticated and helpful contract exists, made specifically for the Chicago community of Realtors, Home/property owners and their tenants, why is it not publicly available?

I am seeing some delinquencies that show foreclosure, but the numbers don't make sense unless there is some sort of ground rent or non-mortgage loan tied up with the properties.