New(ish) to Real Estate

Hi all!

I'm from the Ottawa, ON area and I plan to buy my first (sort of) rental property.  Let me explain.  In 2016, I bought my first house for 200k.  During that time, I have always either had a roommate helping to cover cost of rent/bills.  Over the last year and a half, I've been doing travel nursing which has allowed me to rent out my house (single family bungalow).  With this house, i'm only charging 1700$/month (all included), which by the end of the year i'm technically paying 2500$ out of pocket.  However, these are incredible tenants, who paint/fix/treat the property exceptionally well, and I prefer to have them paying what they can afford.  Just for context, I spoke with a realtor and got comparables, and my place could technically be rented out for 2-2200$/month (not incl utilities).

The second thing, is within the next few months i'm working with my dad to figure out how to go about buying his duplex. Currently the plan is to have the place inspected, speak with a professional accountant, and a lawyer about our plan and to identify the best way to go ahead with the purchase. What we would like to do is for me to buy his place for the price of the remainder of his mortgage, around 60k (30k out of pocket, 30k HELOC) and for X amount of years give him X amount of dollars per month as an agreement. This to me seems like an incredible opportunity, the duplex is worth 425-450k. My dad is very frugal, retired, and wouldn't be able to afford any fixes to the house if they were needed. For example, if he needed a new roof he wouldn't be able to afford it, and as a result he would need to put the house up for purchase and move out. However, I could. This would allow him to continue to live there and still be independent and live in his home for as long as he could. Side note to this duplex is, my dad would live downstairs (paying only cable/internet/what have you). The tenants upstairs currently pay 800$/month, but cover their own gas/electric/internet/etc. Also they're my aunt/uncle, who are also retired and up in age. They probably could only live there for the next couple of years before likely needing to move. To add, the top portion of the duplex I could get about 1300$/month (estimating) and 1.6-2k (estimating again) for the downstairs.

Clearly, with both properties i'm not really going to be making any money, however i'll have equity and as mentioned I still have a job where I make good money.  But also eventually once my dad/aunt/uncle move out i could have good cash flow from the duplex (same with my house if current tenants ever moved).

I guess a question I have is, have any of you been in this situation before?  Where you aren't really making cash flow off your properties but that you felt okay with it because of the tenants ?  In addition, has anyone done something similar to what me and my father are planning?  Either way we will be discussing it with professionals , but curious to other peoples experiences of similar situation!