Here is the rule from the IRS regarding length of stay for short term rentals:As defined by Treasury Regulation Sec. 1.469-1T(e)(3)(ii)(A)The average period of customer use is 7 days or lessThe average period of customer use is 30 days or less.

The emotional part takes time to develop, but the more you consciously practice it, the better.  

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.

Update: We ended up backing out of the commercial deal, way too many issues going on and shady practices that we were not comfortable engaging with.Now the question is what to do with the chunk of money left after we pay taxes.

Just double-check with the Illinois Department of Financial and Professional Regulation (IDFPR) to make sure you have all the specifics covered.Managing Broker and Deal Visibility: Yes, typically if you hold your license under a managing broker, they’ll have visibility into your deals since they're ultimately responsible for the transactions you complete.

Practice running the numbers.

Ensure it cash flows comfortably.Market & Location: Research local rental demand, property values, and any applicable LTR regulations to understand the area’s potential for long-term success.Future Potential: Consider if the property could appreciate or attract quality tenants over time, supporting stable cash flow and asset growth.This checklist should set you up for a solid LTR investment!

However, based on regulations, only Seattle and San Jose allows you to have two separate parcel numbers.

Now, I know someone could say the cost should be "negligible" couple of hundred dollars a month, in comparison to the whole buildout budget, but still I do want to know what are the best practices out there.

In practice how Mello Roos works is you create a political subdivision and apply to the county they approve the area for the Bond issue.. you need Bond council and a investment bank to create and sell the bonds. once the Bond issue is approved this allows the developer to get a Bridge loan to build said improvements ( that are usually 5 to 50 million or so) Once improvements are in  and taken over by the county the Bond money is released and is used to pay off the Bridge lender..