For instance, the term could be 3 years and add a clause that says they have to return the property to the condition it was in when they moved in, not just keep their deposit. 

Any tips you could give me on this in terms of viability?

I am thinking of starting with rentals, be it short term, midterm or longterm. 

Been doing wholesaling off and on with little success but hopefully more time to devote to that shortly.

You'd be surprised to learn that someone living in a rental or apartment, that has a family and is a successful small businessman, has the money and is willing to take that deal.

My focus is on providing either turnkey-style space for those interested in temporary, infrequent use or long-term leasing for business folks who require conference room space (or perhaps event space).

With that said, the income can still offset the cost of holding the property as a long-term investment.

That is tight leverage for an investment 2nd position loan.A private investor might be willing to do it, it's not going to be cheap at all & will be short-term money & will not be a line of credit to take out at your liking.What is your rate on the 1st?

I feel like my "circle of people" really needs an expansion and improvement and I want someone with more experience in the field I want to be in to really help me gain myself to success!

I'd underwrite the property, with that low interest rate assumable mortgage, to cash flow positively from day 1 as a long-term rental, but be willing and able to use the rent by the room strategy or to rent out part of the property as a Short Term Rental to dramatically increase cash flow during my occupancy.