You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

Hence, your goal should be staying on the first page as long as possible instead of picking up a few bookings from different places.  

Hello, I am graduating soon and I have the opportunity to either stay in Boston or Miami.

He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

Personally, I like to update it weekly—it helps me stay on top of things and, honestly, I find it fun!

I’m curious - are you leaning toward staying local in Connecticut, or are you open to exploring oppurtunities in out-of-state markets like Phoenix?

I see 3-5 as a fad.Fractional ownership - way to much overhead for these to be profitable. think "timeshare".STR in non traditional markets - running a STR is a business and real estate, boils down to location location location - who would want to go to a conference and stay in a STR vs. the hotel where the conference is at, most businesses pay for this I do not see why.Mixed use with green - this has been going on for years- it will continue but it is also more expensive to build - which means higher costs to use.Not trying to be debbie downer, I have seen these attempted to be done in the past and they really have not been successful.I do really like the BTR model though as I continue to see that as a very good option in the future. 

Otherwise with the dwindling tech sector in SF, and the remote work (2-3 days a week) that is most likely here to stay, it just doesn't seem like a strong mid term market to me.

We offered our impacted tenants a hotel room while we were awaiting repairs, but both tenants decided it was easier to stay put. 

Generally in Illinois, the Tenant does not have the right to cure the lease violation and stay in the property.