This sets the right expectations. 

Weigh convenience vs. control—your renovations and location set you up well for long-term growth! 

Sounds like you set yourselves up for success, and it’s paying off!

For this reason, I teach people to set policies for renting to unrelated individuals.

It’s humbing and frustrating, but it also teaches you those guardrails you’ll want next time.. like thorough screening, a solid lease agreement that sets ground rules upfront, and maybe even setting aside a bit more cushion in reserves.Chicago’s got plenty of investor-friendly pockets.

The out of the box strategies and set ups sold will never replace customized AP/Tax strategies based on individualized circumstances. 

These are two entirely different worlds that need two completely different skill sets to effectively manage.

My long-term goal would be investing in large scale hotels, I know I know, that's quite ambitious, but I don't mind starting small and working my way up there, as long as I start from somewhere!

You can also split the difference by looking at the historic energy usage for the property and setting that as a utility 'cap.'

We both knew we were aligned in our goals and had a clear understanding of our respective roles in the deal from the outset.If seller financing is part of the equation, look for someone who’s not only experienced with creative financing but also understands how to manage the potential risks involved.