Hi @Vivien Martin - Glad to have you here as part of the BP Community now!

My Chicago mentality has only grown because I continue to grow and build a stronger network of A players here in the city!

The other concern I have is service life. 

Yet the payment processor is issuing the 1099-K to the property management company.

The transition isn't just about property size; it's about shifting your entire approach.I've observed that successful transitions typically happen when investors have:- Stabilized 5-7 single-family rentals with systems in place- Built relationships with at least 2-3 reliable lenders- Established a maintenance crew that can handle larger projects- Accumulated at least 6 months of operating expenses as reservesI asked a client of mine who owns a 420-unit multi-family in Nevada how he started his RE investment journey, and he told me that he started with a duplex in Buena Park, CA, 40 years ago and used the 1031 exchange to grow his portfolio to 420 units, never paid taxes on sale of any of his properties.The most seamless path I've seen starts with small multi-family (5-10 units) rather than jumping straight to 50+ units.

After doing a handful you will get the hang of running numbers quick.The poster @Tyler Hall outlined some good steps above.

So Augusta, GA is one of the locations that has been on the top of my list.  

My state is very fair to landlords, but there's no way to win this scenario.

With time and persistence, it can provide the kind of financial freedom many people only dream of.

Until the conditional use permit is applied for, an operator of a short-term rental is required to apply for a short-term rental permit.