The key is to find a niche, like near that gun range, and to provide a "wow factor", like an in ground pool, game room, near a park, a natural preserve, etc.

We went through a title company and the building is now appearing in my name on county records.

I have heard mixed reviews of re-titling into an LLC and risking the "due on sale" clause in my mortgages. 

As of now, we plan on having a robust written agreement and I'm looking for advice on the proper structure (LP, GP) and how it plays into the mortgage, liabilities, holding title, etc.Thank you in advance for your help!

The bank doesn't know or care because they're receiving the mortgage payments on time and there's no change of title or anything.Here's my plan.......Can I purchase a second residence/vacation condo? 

You cannot take title in an LLC at the closing table.

Not saying it's not possible, but this is likely the hangup. buying cash and then cash-out refi is easy and done all day, even with commercial loans, but likely all will want you to carry some liability in some form (skin in the game) that said, I'm just one lender I can't speak for all of them

I can concur that tenant occupied properties tend to give me a harder time with negotiations but at the end of the day it’s a numbers game so I go after it like any other lead.

You can even have an attorney available 24/7 for less than $40.00 a month.TITLE: Since you live in Illinois you should use an Illinois Land Trust to take title to all future purchases.

Like find a good title company, good realtor, accountant, contractors for rehabs, Escrow company, etc.