My original intention was to flip the property and use the proceeds to help purchase a small multi-family home but am now considering holding the Single Family property as a rental.  

By being in Boulder, you have the perfect opportunity to take advantage of the college rental market & rent out your extra rooms to college kids in the area. 

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

My name is Jack and my partners and I just acquired some rental properties in Cape Breton recently as we view there being an opportunity for growth in that market.

Hello - I own a duplex in Bracebridge, Ontario, Canada - the largest issue I have has been property management - I live in BC, and there are not many property management companies in Muskoka that handle long term rentals - many do air bnb properties, but most property owners who rent long term do the management on their own. 

Our rental has very different demands than yours does.Thanks in advance!

If you want double entry accounting, flexibility, and solid support, REI will allow you to manage your rentals on your own. 

Hey John I am just new to wholesaling and I want to start wholesaling but every video I saw or book I read on wholesaling says to not mention to the seller we are wholesalers, but probably is better off for everyone to be honest about what I am trying to do with the property, no matter if I am looking to assign it, do a 1031 exchange, use it as a rental, etc.

MLS - negotiated backwards based on rental income available.

I have the similar settings as @Bruce Woodruff "guest must have a good track record" and I send a pre-book message that they will have to provide me with their email address in order for me to send them the rental agreement and I have not had any issues with using that option.