If you are okay with someone painting over your original woodwork (even though the lease says they can't) or ruining your marble countertops when they dye their hair (true stories) then you may be emotionally hardened enough to rent your original home that you have lovingly designed.Consider, also that at times you will have to carry two large mortgage payments and decide if you are willing to do that.

The challenge for present day investors is with elevated mortgage rates and record high housing prices, the carrying costs and incentive to invest now can be restrictive. 

Carrie Douglas is in a STR mastermind with us and knows Wisconsin.

What sort of insurance does the manager carry to make sure she can make you whole should things go wrong?

I will use hard money and private money but always borrow the money responsibly and under that every deal carries risks and there are no guranteed returns. 

I own a four-plex that has a contract with Dadson Laundry that carried over from the previous owner.

You can get buildings that will carry themselves while you turn them around.

I had negotiated a substitution of collateral clause in the purchase agreement, that stated I could substitute a note that (1) yielded the same or more and (2) carried the same or less risk.  

Not only that but you are going to carry a Heloc in a 2nd lien position and you will not be able to pull out more cash unless you do a cash out refinance to pay off the previous Heloc and take out more cash.85% of the home owners who take out a Heloc refinance in 3-5 years so it makes more sense to simply do a COR and avoid the future closing costs.

@Carrie Zhang Interesting you found additional experiences on that reddit thread - thx for sharing!