A few updates that didn't fit into the above post:The attorney who handled our closing offered to assist the sellers pro-bono in an effort to recover some of the equity.

This will provide consistency and clarity in how you handle your properties.Start by reviewing your current Property Management (PM) agreement.

I’m almost hoping she rejects my offer because it’s so complicated, but it kinda seems like it could be a win win.We pay $2600/monthI’d offer her $3k/month ($600k @5% 30year amortization) plus I handle taxes and insurance.

I have two units separately metered and we are installing a shared washer and dryer. Logistically, the water and power for the dryer would come from the smaller one bedroom and the washer power would come from the 2-B...

If you spend it now, you lose your leverage for the rest of the lease, and you'll have nothing to handle unpaid rent, cleaning, or repairs after termination.You are starting down a dangerous path.

Thanks guys - my partner does the Brokerage and we were discussing how to address the commission - we are fine paying just debating how to handle the upfront question when the Buyers agent calls about the listing ...My thoughts were to simply state that Seller is fine paying a commission and put it in the offer - and he wants to offer the % upfront ... 

LLC’s provide them no shield here.So, would-be syndicators, please take note:  please treat this business like a loaded weapon:  Handled carefully and with training and experience it can save your life.

That said, if you can comfortably handle the additional down payment and monthly payment consequences of a higher purchase price (and the lenders agree), and you have a few different good options with the property then it could be a wise investment.By a few good options . . . you want to have some exit strategy other than STR that will work in case the something happens to make STR uncouth in your area. 

I have been doing the property management and leasing myself, while sometimes trying to handle maintenance.   

@Camila Cabrera just DMed you a great Dupage eviction attorney who handles Chicago and suburbs!