One was taken over by some squatters causing problems for the neighbors and the police were contacted who contacted the lender.

And even if the tenants chooses to stay in your property for 2yrs, the damage they may cause will eat away all of your cash flow and leave you potentially upside down.

It might cause me financial harm as I have to sell more stocks and might pay short term capital gains vs long term capital gains.

Another common problem is poor due diligence—jumping into deals without verifying the borrower or collateral often leads to future regrets.I’ve also seen over-leveraged borrowers cause trouble, prioritizing other creditors over private lenders.

yeah the tenant pushing back is my concern. it just so happened that this happened with the tenant that seems to not like paying. and the heating is electric and this winter has been extremely cold which caused the electric bill to jump up to $800!

@Russell Brazil He closed his account, cause he needs to eat a lot of crow.   

Working with AvantStay caused me large ongoing financial losses.I signed on with them to manage two of my properties in vacation markets.

I would limit the open calendar days on VRBO to maybe only 30 or so out so as to not cause any/many issues (having too many dates show as booked) when I subsequently go live on Airbnb.

We have a high saturation of rentals that has caused the market to lose money. 

It can be done and people do it, but to start out not knowing what is necessary will very probably cause you to lose money, to say the least.