My partner and I are eager to embark on our first real estate venture by acquiring a long-term rental apartment in downtown Chicago.

Now, I have a portfolio of Short Term Rentals and Long Term Rentals.

Most people just use the term but there is association management, apartment/ Multi-family management and then property management.For instance, in Florida, you need a license to practice Association Management (in most cases) and a real estate license to practice property management (in most cases). 

Hello all,Would love to hear your thoughts on whether there is a beach town that allows short term rentals in California, and where the following plan may make sense. 

In this case, rates don't matter as much as lower closing costs, since it would be short-term.  

Can anyone point me towards a private money lender offering these terms ? 

Not buying/selling for others like an agent would do.Think more like get a rental or two or a short term rental to get those hours.

@Daniel Purcell I have a 3-plex uptown that is zoned HU-MU my understanding is that I can rent 1 out through short term rentals even without a Homestead excemption.

I've thought of many different angels, but still not sure why this project was special/different or offering different terms.   

Also, probably I'd have to fly out to KC a few times until I buy the property to meet the team, potential properties, etc which will add to the costs (~$600-$800 each trip) of owning an OOS property.Given this market, I'd like to hear from OOS investors if they think it's still doable to pull off an purchase worth investing in.I don't want to talk myself out of it again and focus on the negatives but also, want to make a sound decision that benefits me in the long term and doesn't hurt [much] in the short term.