The building is located in Berwyn, IL... just outside "Chicago Proper" where STR licensing isn't required.

It sounds like if appreciation is the main goal that will open up different markets for you that will require more capital to gain that appreciation. 

I also got lucky and found a group of people to help me with the eviction, as the sheriff requires a minimum of eight people to do the eviction when it takes place.

One of the requirements is to have a trustee. selecting a friend/family isn’t an option for me.

Apparently our DTI is too high for the HELOC so we can do a cash out refi but that is less desirable because it means we cannot then get the loan for the rental property despite having 25% down.

If you ask the manager to justify a fee and he starts hemming and hawing, move on or require them to remove the fee.

Our documents are always up to date with the most current legal requirements and are specialized disclosures are designed to protect the lenders interest no matter what type of loan you are making.

Just wanted to share, I've noticed a loosening in down payment requirements for DSCR (debt service ratio loans) that either use the actual or proposed rental income to qualify.

Should I require both of them to pay application fee or only one fee?

@Cynthia Fuentes reality check you may not want to hear:How will you succeed when you've been in the business for 11 years, but don't know the licensing requirements - or a better place to research than asking a bunch of strangers?