It's amazing how cheap it can get when you're paying physical cash and having your contractor pick it up at the warehouse.

If the deal is right you can use hard/ private money to finance the home purchase and some or all of the repairs, then do a cash out refinance to pay off your hard/private money. 

They pay for it. 

I would also share pros and cons of paying taxes on the windfall versus owner carry.

It takes a couple of calls to schedule, then they pay the invoice.

Option 2: We pay cash to build a small 2/2 cabin initially.

The price you pay for being part of the Disney World spoon-feed of guests is that the barrier to entry for profitable STRs (ones that leverage close to or max LTV) is very, very high.  

You will get some of these as well (This inquiry was for one of my 1500 SF 2 Bed + home office units)..... but by no means does this investment strategy warrant paying for a course.

.- Cities like Toronto will levy another tax (Vacant Home tax) equivalent to 1% of the current assessed value of the property if the property is not occupied (rented, owner-occupied, family occupied, all count as occupied)- Land Transfer Tax: while the Province of Ontario charges anywhere between 0.5 - 2% of Land Transfer Tax when your transaction closes, you should expect to pay this amount twice if the property is in the City of Toronto .

They will pay a higher mortgage payment because they are not trying to cash flow.