The only thing I can think of that may be harder to deal with if I am not local is routine maintenance issues, but I was thinking I can just ask around for some handy man referrals to have at the ready in case those smaller issues arise, while I would instruct our future tenants to contact our service provider for any emergency issues. 

Id love some input on starting my own property management business to generate cash for more deals.

It was more to have another cool place to vacation and let it pay for itself and appreciate.I never plan on selling either property.If I see a great deal on a beach house that will be next.

Hey @Teekap Pate - Many condo deals in that area of Chicago get killed by the outrageous HOA fees. 

Ideally there would be a number for tenants to call, they would take the calls and deal with them.

The 3 states I work primarily in already require buyer agency agreements by state law. 50% of our deals are off market, so our commissions already got written into our offers as a standard operating procedure.So virtually no changes for me. 

What made you interested in investing in this type of deal?

I also had a private investor on the deal (who I just paid off separately) and the numbers looked good to her as well. 

You can pivot based off the neighborhoods whether you want more appreciating deals or better cash flow, I have a mixed portfolio worth about 2.5m.Let's chat i'd love to help guide you and possibly serve you with your real estate needs.

Again I’m no expert I just know that rent stabilized is rough for owners of properties, do your own research on them and 1 unit in a building should not make or break the deal unless your really squeezing numbers.