I am a dentist from Louisiana who does real estate as a long term investment.

That is why there are so many shared homes.1 hour away from full weekends of sport, dentist,  friends is like moving to another state and the gas costs don't help. 

You have doctors, a dentist, real estate agents, lawyers and other people who you know.

I am a dentist. 

I started racing right out of high school, so no college degree which eliminates doctor/lawyer/cpa/dentist/stockbroker...

Maybe I could get someone to transfer me the money and I could pay a good interest on it for a year, because I do work with a dentist now that will be in Buffalo with me; he is going to help me into dental school.

I get it... some people are dumb and might end up accidentally blocking their vacation rental when they have a dentist appointment or something if they sync the wrong calender.

Just a thought if your choosing the PM route, chose like you would your dentist or doctor. 

You seem like the poster child for the people who are least in need of going to the dentist are the one who go and the ones who don't need to do.

Check out this section from IRS.gov:People such as doctors, dentists, veterinarians, lawyers, accountants, contractors, subcontractors, public stenographers, or auctioneers who are in an independent trade, business, or profession in which they offer their services to the general public are generally independent contractors.