Quote from @Alan Asriants: Here is a note I found from Fannie mae: ADUs are not eligible with a 2-4 unit dwelling, or when a manufactured home is the primary residence.

Since you are renting out part of your primary residence in Maryland, your main concerns should be liability protection and tax compliance rather than complex asset structures.

Investment Info:Single-family residence wholesale investment.

However while people in Windsor doesn't have the luxury of high paying jobs that GTA residents have, is it just a temporary fever of buying houses, or there is really something going on in this city ? 

Investment Info:Single-family residence fix & flip investment.

Keep in touch with your lending partners for each one so you can understand whether you need departure residence income to qualify for the next or not.Finally, if you're investing with a Significant other, I recommend considering a "leapfrog" strategy where you buy one, then your partner buys the next, and so on.  

Investment Info:Single-family residence wholesale investment.

Investment Info:Single-family residence fix & flip investment.

But the manager's unit is really a 3000 sqft / 4 br / 2.5 ba SFR, and we live there as our primary residence. 

This may be to deliberately prevent discovery of other electrical issues or prevent fire/injury.You will need some form of hard money or construction financing to purchase the property as is, and you will need to get the property occupant-ready to pass an appraisal before permanent financing is on the table.