Adding 16 small units can be very profitable, with enough profit for all those involved.  

There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

It’s a balancing act of controlling costs while also controlling risk of personal injury to your tenants and property visitors as well as maintaining goodwill with all involved at the properties. 

Two flats are essentially just houses.... they trade like houses and there is a lot of emotion involved.

So for example, let's say a friend of mine wants to get involved in real estate but doesn't have the time, knowledge, experience, or resources to do it very well.

Its doubtful that the municipalities involved would sign off on a condo conversion or subdivision, as their aren't many rentals in the area.

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

These leads were very unresponsive and may pan out over a longer period of time but the time involved is just not worth the effort.  

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

That covers the down payment for the purchase, the rehab, and the $18,000 for reserves for the account, and $5,000 for me for each property for the time and work involved.