Multi-Family, IOS, house flipping and later on property development.

The most important part is the team. if you can build a killer team of handymen, cleaner, and a couple trades you can manage anywhere.

People with integrity will NOT be offended to put everything in writing to protect both parties.

Keep the beautiful images of your STR up and looking charming, set up your own free website with videos, photos of activities in the area, lists of restaurants, hiking, historic whatever.

I am involved with quite a few mix-use and multi-family projects where historically bank originated construction to permanent financing was used.

She's got a lot of YouTube videos about midterm rentals and does consulting with new MTR buyers. 

I invest in B class multi unit properties with positive cash flow and where value/appreciation is driven by the rental income not by home buyers.

This is not as nice and sits for a while on the market, the hard part is getting the sellers to come to the reality that their home is not worth what they think.

My new STR property is owned by a multi-member LLC (consisting of my family members). 

I have already secured renters and am very excited to get started.Regarding the Chicago market, I have come to understand that there is an abundance of multi-family properties, but it is important to note the property taxes outside the city limits can be very high.