Been in the area twice now and driven around to get a better feel.

Understand taxes are a part of every transaction and create friction by introducing additional concerns.Tax planning stems from there being a lack of neutrality in the tax system.Anytime there is an alternative treatment of a transaction across taxpayers, tax rates, tax character, timing, jurisdiction, etc., you have a planning opportunity.Practice manipulating key variables to create alternatives - generally in one of three ways, shifting across periods, shifting across taxpayers, or converting the character.No one actually uses the word loophole in accounting.For example, what the hell is a STR loophole?

So, does anyone have recommendations for an app with built-in optical character recognition, logical UI, and easy-to-learn functions?

And the IRS does do this.Here are some factors from a case.In determining whether the income should be classified as ordinary income or capital gain, the court evaluated nine criteria: (1) the taxpayer’s purpose in acquiring the property; (2) the purpose for which the property was subsequently held; (3) the taxpayer’s everyday business and the relationship of the income from the property to the taxpayer’s total income; (4) the frequency, continuity, and substantiality of sales of property; (5) the extent of developing and improving the property to increase sales revenue; (6) the extent to which the taxpayer used advertising, promotion, or other activities to increase sales; (7) the use of a business office for the sale of property; (8) the character and degree of supervision or control the taxpayer exercised over any representative selling the property; and (9) the time and effort the taxpayer habitually devoted to sales of property.

It's a character test. 

However, these factors have been masked by elevated sales volume in 23Q1, which was largely driven by sales of properties within city limits as a hefty transfer tax was imposed at the start of April for properties within the city of Los Angeles.

The result was driven by the asset being a creative office conversion that finished in 2017 (latest generation space), was 100% leased, and was in a strong location in Santa Monica, historically one of L.A.'

Like all real estate it’s market driven.  

Should I have driven to find and vet the contractor sooner on my own?

The real question now is, where and what team can bring us the most compelling as well as data driven analytics to make the best decision.