First, I want to the Express my Gratitude to God in advance for the amazing thinks he has in the future for me: The Inspirations He will send my way during prayers and meditations; The blessings and guidance in my daily encounters; The amazing time to look forward to with family and friends; The Fruitful relationships I will continue to develop with my patients, clients, coworkers, fellow investors and entrepreneurs, and all other professionals; Abundant spiritual, mental, physical and social health; The constant awareness that “I don't wanna spend my whole life asking, What if I had given everything, Instead of going through the motions?”

I have an applicant for my one-bedroom shared condo who lists his job as a property manager for a company that he owns.This property generally attracts college students and millennials just starting out.Why would a 50+ real estate professional want to rent from me?

Hire a Professional Company!

The point being is that to find the right attorney or anyone else you need in a professional capacity , you have to ask around, and get involved. 

Seems like a very professional environment.

Fair warning here - typically, you will get young professionals as roommates in this situation, but the numbers typically do work better than the multifamily properties. 

Professionalism is a matter of HOW you do something, not HOW MUCH TIME you spend doing it.

We had a friend who was well into retirement years, their early 80s, and he and his wife still had about 20 units - it was their 'retirement thing' when they both retired early from their professional careers.

I have been calling contractors all week but either they are too busy or aren't professional enough.

What he ended up doing after pondering on what to do is be more Pro-Active thinking on selecting who lives Upstairs and Downstairs..Typically families w Kids or pets he rented downstairs, young Professionals he rented Upstairs.