This can be done using accounting software or a spreadsheet, which can make it easier to collate and organize the information you need for 1099 filing.It's important to review the IRS guidelines and requirements for 1099s annually to ensure compliance.

If a buyer has cash, that works, or owner willing to take back 2nd....but I've had trouble finding a lender who will take a 2nd on the gap.   

This is what many get tripped up on when they review syndications and I suspect many would make different investment decisions if they didn't focus so narrowly on dividends and ownership interest. 

property is @ 550k Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

This is more in commercial deals less in residential to have an attorney to review the contract that's other than the real estate agent who represent you since commercial deals are generally much higher stake in it.

In the income example maybe there is a way to look at it pre-tax on gross income for what we declare to a lender etc as our actual earned overall income; and maybe some prefer to look at net income after taxes.  

Since I posted this, I have had a few conversations with my mentor and other real estate investors/lenders and have a much better grasp on action items when the right deal comes along.

You can boost your ADR by optimizing listing details, adjusting pricing based on market data, improving property appeal, and leveraging positive reviews.

I personally recommend that if you have good debt on the first one to take a heloc, and if your debt is meh to potentially look into cashout refi’ing on the 1st building and keeping your eyes open for the next opportunity :) Analyze both accordingly and talk to your lender as well as other investors to get their thoughts! 

AI sounds great, but I don't see a track record of success and every time I google the company the reviews are not great.