@Michael Overall, The length of time that a DST is open is going to keep you from doing this over time like @Jon Taylor said. 

The truth is, they will keep playing games and milk you for every penny they can, then they will leave the house a mess and cost more with cleaning, repairs, and vacancy.

However, after you get some experience, you probably want to get a Private Lender since this will allow you to keep the majority of the profits.

To avoid going through the same poor experience, keep reading.Even if someone give you a referral, don’t make the mistake of assuming that PMC will meet your expectations, just because they met the expectations of the referral source.We also can’t believe how many owners hire the first PMC they speak with!

No but keep track of those repairs as it will add to your cost basis when you go to sell it and have to pay capital gains.

I keep saying it's making me a better investor and that's probably true.

Lake Geneva and Walworth county is beautiful, they keep it pretty clean with  strict conservation and zoning... 

Thank you.Let's keep in touch.

For bookkeeping purposes, I recommend designating a separate bank account exclusive to the house hack activities to keep some sanity.

Keep in mind it is a risk and speculation, if something happens(market tanks, job loss, etc) then you will be out money.