Most people will tell you that your second choice can't be done, but the IRS has issued two (2) Private Letter Rulings on point where they did allow the taxpayer to build on property they already owned through a 1031 Exchange. 

Take a free an clear property, pull half of the equity out (tax free) and invest that for example in the stock market.5k-10k in monthly income after everything sounds like 20-30 units.

Your acquisition fee can be "exchanged" for your equity contribution.  

That’s far better than they can make in the volatile stock market  annualized year after year in cash flow alone.

However, newer properties don’t always cash flow well, and you’re giving up significant equity in exchange for a home that might not provide you much financial gain immediately.

One thing I did was create templates for different types of investments, stocks, crypto, so I can quickly update them without creating new docs from scratch each time.If you're open to trying something new, I’ve also used Excel, especially with its built-in templates for tracking finances.

This exclusion allows you to reinvest the proceeds from the sale of your primary residence without being immediately taxed on the capital gains.However, it seems like you might be considering a Section 1031 exchange based on how your question is phrased.

In a court situation, would email communication suffice for appropriate documentation for daily exchange?

In your case though, I've heard of people in Denver proper with duplexes who parter with LTR tenants (you could put them in the basement) who will co-host with you and be able to get a STR permit since it's their primary residence and you can work out a profit split for the STR or some kind of reduced rent for your LTR in exchange for helping you and you being able to keep the STR runningJust a creative idea I wanted to toss out as a potential plan B or plan C!

According to people who study the stock market, there is a common theme, "buy the rumor, sell the news."