Don’t put everything in one deal, with one sponsor, or only one type of property.  

The tenant wants to stay another 2 years.My other adult properties have often had long-term tenants.

If not I wouldn't bother selling as there is an incredible amount of money lost in buying and selling properties, so you have to make sure you have a plan to maximize the equity and actually have enough. 

Four properties were existing STR's that had a permit 'transfer' and the other half were eligible properties that successfully launched with astounding success.

High-end properties might require a white-glove approach with customized services, while more modest properties may prioritize affordability and efficient communication.

@Brett Riemensniderwe don't know all the details, but as i said that's a very expensive way to buy property - if you can't afford a property without overleveraging then you might just have to save up more.

It is definitely a bit more tricky on an investment property, but it can for sure be done.What area of Chicago is the property in?

The best amenities for Airbnb in terms of ROI often depend on your target audience and the location of your property.

I know a common practice (at least for syndications), is to create a separate LLC for the property and then raise capital once the deal is already under contract.

Quote from @Brendan Jones: For the homes, and or properties that you will use as a primary or a rental property one big thing I look for is infrastructure in the area, extrinsic value (I.e. hospitals in the area, schools, and job market), and the last thing is creature comforts for people (I.e. is a store to get groceries 1 hour away or 2 minutes away).