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.

Example, front exterior, front door, inside entry.. etc.

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.

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...

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 ... 

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.   

However, its downfall (and really what makes it so easy) is that it is a single-entry system.

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

We're currently looking for ways to streamline supplies for cleaners (toiletries, towels, item replacements) and handle small handyman issues.