Gino Our major presence is in one market.We have an in-house Construction Arm that travels to between our main market and some satellite markets.We build and vet property management teams in Satellite markets before taking down deals there.

So with all that, I'm thinking to open booking now for next summer with a 7 day minimum, see how it books out, and by late winter/spring I can reduce it to a 3 day min to fill any remaining weekends, and then work on filling mid-week vacancies as summer approaches.We were leaning towards Fri-Fri, but Michael I like your suggestion about the Mon-Mon option, which could be nice because renters would have the weekend to travel and then begin their stay on a Monday, then they would end their stay on an upnote with a long weekend...But with either Fri-Fri or Mon-Mon renters would probably need to take 6 days off work...Sunday-Sunday might actually be better because renters would only need 5 days off.  

I work random jobs and/or travel May-November. 

It’s essential to make your property appealing to traveling professionals, such as nurses or corporate employees.

Anything west of those areas (excluding Speedway $$$) will be D class, no new construction/flips, and I don't travel though. 

I’m looking to get a condo 2bd/1bath or something similar near rush, Stroger/CC hospital, and UIC (not just looking to attract travel nurses I promise lol).

Medical costs....

This is what the site is made for, as well as for insurance displacement, travel nurses, etc.

I travel a lot to all my clients back east so I do get out to fine dining on those trips..

Perhaps not the best example, but  what you are doing is no different than a medical patient who walks into 6 doctors offices with a broken finger asking to be treated with radiation.