The issues I ran into was the local market was already flooded with STR's and in order to be profitable you had to stand out with a home that was either near an attraction (ie great view, Garden of the Gods, Downtown, or a College) or the unit had to have amenities (Hot tub, Instagram Wall, Pickle Ball Court) that would place your listing far and above other similar listings.I think you should strongly consider if you more interested in moving away and starting a life somewhere else, or in creating a cash flowing investment to supplement your income? 

(Finding deals, the lending landscape/rates, etc).

10DefineConsult an exterior designer (outside of house and landscape) (is this needed?)

If you have a multi-family property, then you have to figure out how to make the tenants share the responsibility or you hire someone to handle it for them.You have to consider insulation, maintenance of weather stripping on doors and windows, servicing the boiler/furnace, winterizing sprinkler systems, disconnecting garden hoses from hose bibs, and much more.It's very risky to manage rentals from a distance.

New carpet/flooring, paint, fix-its, a new drive-way and landscaping updates, and quite a few appliances over the portfolio. 

I'm particularly passionate about New Brunswick and Ontario.Outside of real estate, I enjoy gardening, hiking, cooking, and travling.Excited to learn and connect with you all!

On the other hand, if a client hires RES at the tail-end of an existing lease and knows full well that their rental property is falling apart and needs everything from paint, flooring, blinds, other repairs, landscaping, etc., we will not under any circumstances spearhead this project.

But I am getting single mothers who are wanting to rent , BUT when they realize they have to cut the grass or pay a landscape company they dont want it . 

In my expensive market I've seen folks get creative by renting gardening space, Ie raised beds,some tools.

We're planning on making quite a few updates to the property, like putting in patios for each unit, fencing, landscaping, etc.