Regarding the payout inefficiencies, I remember the nightmare that some folks were experiencing with state unemployment benefits during Covid.

Hospitality, attention to detail, cleaning/handyman team, programs used for bookings and calendar organization, inventory audits, home maintenance, etc. are all extremely important but all of that doesn't even begin to describe all of the things an experienced property manager does.It is a matter of how much time and energy you have to invest in your properties and if that time and energy is worth it to you.

. $150 cash flow on any rental especially a triplex is dangerzone imo. 1 month of vacancy of 1 unit could destroy a years worth of financial gains.  

This requires a dedicated effort sourcing and analyzing hundreds of deals to find the one or two worth pursuing.  

Your net worth and cash flow goes up exponentially when you tap into your equity to scale up and buy more and more cash flowing properties.

Columbus is worth looking into as well if you want to hold real estate long term.  

I can't speak too much to the market on the Westside, but as far as affordability on the West Coast Spokane is worth looking into.

I just don't know how at the moment, but when that day comes, I'll suddenly remember Nicholas L.

Remember years ago an owner didn't like our pricing, so found their own reject of CL.

Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.