I want to make the best decision while honoring my agreements and maintaining professional integrity in this deal.

Readers should seek professional advice.

I'm seeking an opportunity for a summer home in the area, and would like to rent it in the winter when I'm not there. 

@Jonathan Greene Thank you for that, I will seek out a meet up in my local area.

My overall goal for my professional career is to start an investment firm and own a big multifamily portfolio and get into development.

If it’s rental property do you seek amenities in the locaton or that doesn’t matter.

The challenges are Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Please let me know who you have worked with and why you like them (How many properties do they manage for you, how long have you worked with them, what you like about them etc.)When the unit is vacant, do they cover the cost for professional photography to rent it out again, or is that an additional fee? 

Most of them do not and can even hurt you - as your S-corp with rentals. yeah this was under the guidance of the tax professional i went to.

I use Stessa for accounting, I love it, it links right to my bank account/credit card accounts and I can assign purchases to different properties and units of the property for multi-unit properties and at the end of the year I have a simple report to give my tax professional