It's very expensive, has horrible traffic on restrictive roads due to the geography, but is very beautiful, not much snow, milder temperature swings, great hiking and outdoor activities such as 4x4 or hot air balloon tours - very touristy.  

I'm now working on my second "dive into full-time REI" hahaThe first time I thought that I would be able to generate cashflow out of thin air and that I could half-*** my side gig of being an RE agent for investors. 

We are thinking of doing Air BnB to rent it out and I have looked at what's out there on Air BnB, HomeAway, FlipKey and other sites to see if similar homes are rented out yet for summer 2018 and it appears they are all still not rented out yet.

@Grace Santos what you can do, although tedious, is gather AirDNA comparables and then use google maps street view to see what the actual address is and send the address, the Air BnB listing, and the AirDNA printout for those specific comparables to the appraiser. 

In reality what happens is you end up paying more for a "clean house" but because you are doing a flip people want new mechanicals (central air, 200 amp electric, pvc plumbing stack) so you end up doing a full gut or larger rehab then simple cosmetics and now your returns have shrunk.In your situation for your first investment I would be ok with a smaller return because of the experience gained, but for the next look for larger profit.

@Benjamin Aaker is on the money.Your income probably prevents you from using RE to offset your W2 income but you can still use deductions and depreciation to offset rental income.If you are looking to REI to reduce your taxable income on your W2 earnings REI won’t help much at all.One needs to be precise when discussing tax law.

I'm nervous because I've never had a business before and I still have a full-time job as a cloud solutions architect, which I'm really passionate about - so hopefully it won't be my golden handcuffs that may prevent me to thrive as an investor and  I'm excited because of all the benefits and freedoms being a business owner offers, one of which is to connect and collaborate with forums like this and people like all of you, where I can both learn from and hopefully share later as I develop more experience. :-)

Tough sledding at first, until I took a leap of faith and invested $25,000 into the property to make it more appealing to guests on air bnb and vrbo.

I have read from other that if you are near the ocean the salt air can affect the lock.

As cash is low to even invest in another property in Canada - would courses be a viable option to learn Air BNB arbitrage or STR to potentially earn side income  ?