I can do all the due diligence beforehand, except the soil I have bought a ton of land at auction and tax sales over the last 40 plus years..

Plus it makes bookkeeping and doing taxes etc. more complicated and annoying/ expensive.

What an investor gives up though is tax bene's and the chance ( well at least proforma wise) that you bought at X cap rate and can sell at Y cap rate and there is a big profit that is added on to your returns. 

Non pay of prop tax's non pay of insurance  Waste, etc. 

This type of investment can also offer great tax deduction, depending on your situation.Best of luck on your first deal, feel free to connect with more questions.

When in Due Diligence have a thorough inspection and get estimates for any work that is needed now and potentially in the next 3-5 years. don't forget about the tax benefits to doing the work upfront.

Can anyone recommend software which would accept monthly payments (from me to seller) and create proper 1099 forms for tax purposes at year end? 

If anything it just means that initial newbie tax / buffer is going away. 

Tax structures and mortgage regulations might also shift as canada mortgages are very different.What do you think would happen? 

Does it need to be completed before end of the year to use it when I do taxes in April 2025?