Does the landlord take care of them, or do you as the tenant take care of them?

One thing to be careful with is the last 3 years have been atypical for the Calgary market, it's been a good run, but don't expect these kinds of returns long term.

Be careful, STR are banned in the city of Temecula and fines for violators are $1000/day and can be retroactively enforced. https://temeculaca.gov/1241/Sh...

If you haven't lived there, visited there a lot, or have close friends or relatives there, you may be too detached from the area to pay close attention to it which will lead to PM skimming and just bad oversight on your asset.3.

Even if you could, I don't think a bank would care. 

Focus your attention on creating equity that can be realized through a sale, that's the winning formula.

I am a handyman with a lot of experience in residential and commercial maintenance, so I would like to be close to my first investments so I could take care of the management and repairs myself.

I've spoken with my financial advisor and ran the numbers where spending 5 more years in my W2 sets us up for the future but it's taking all my attention and I can't focus on real estate, plus I’m miserable.

Avoid personal use of the property, as it can limit deductions, and be careful to correctly classify repairs versus capital improvements, as improvements must be depreciated.

My approach is one of careful research, strategic planning, and a willingness to adapt as I grow in this exciting new chapter of my life.