Will use as a family vacation house, and rent it out STR or MTR.

Will use as a family vacation house, and rent it out STR or MTR.

I'm thinking of a short term vacation rental (that'll just be about patching up a family property that happens to be in a heavily touristic area) and then in the future...

I have never owned a home before but I’m considering buying a place here, living in it while I’m here, then short term renting it and using it as a vacation property when I move back to Canada. 

Should you ever have any questions feel free to reach out I enjoy talking REI and heping bigger pockets members with tips and loopholes!

But to touch on some of your points:-Costs to build are probably some of the highest in the nation, other than maybe Telluride or other vacation destinations. 

The time depends on lease length and how long they've been living there.I would also recommend reaching out to their caseworker (if they have one) to let them know the lease will not be renewed.Section 8 voucher holders are incentivized to vacate quickly in order to keep their voucher and avoid having to pay full-market rent out of pocket elsewhere.Hope this helps!

Another lost his primary residence plus his vacation rental and will be staying with me for the next month while he sorts out his home.

The strategies you mentioned above seem to be more advanced strategies, but if that is what you enjoy, learn as much as you can and get into it.With minimal income, I would suggest saving up some money, buying a new primary residence that you can house hack, and keeping your current property as a rental.

Once you transition one of the homes into a full time rental you will reap that benefit by filing a schedule E at the end of the year.There are a few loopholes to consider like calling one home a "Vacation/Second home" which allows you to pull out 80% LTV with a better rate.