It is truly the best way to build generational wealth so props to you for taking the first steps.

Buildium has this statement, hopefully your PMC knows how to generate it.You should be able to give your tax professional the 1099 and annual statement, along with property tax, insurance, etc. bills you personally paid and that's it.I think Buildium even allows the annual statement to be sent in CSV format, so you could just add the expenses you paid to that.

As others have said, it may make more sense to use FHA on a quadplex as you have more units to try and generate income with.

Please DM me if you would like to chat on our current projects  in those areas including market conditions, leads and lead generation.   

These platforms can integrate with your bank accounts, track income and expenses, and generate reports, simplifying your record-keeping.Regular Financial Reviews: Schedule monthly or quarterly reviews of your finances to ensure everything is in order.

It certainly generated some interesting and fun to read dialog.

The 50% rule states that approximately 50% of EGI will typically be consumed by operating expenses.While the 50% rule provides a quick estimate, actual expenses can vary widely depending on the property type, location, age, condition, tenant mix, and market conditions.Here's an example: if a property generates $200,000 in EGI per year, the 50% rule suggests $100,000 would go towards operating expenses like taxes, insurance, utilities, and property management.

My idea was to establish myself with some paid-off, cash flowing properties to make leveraging them for more investments a lot easier.I'd like to flip some houses to generate some cash, but  even knowing what I know I'm struggling to see how to make money doing so. 

Of course, if you then generate additional taxable income, that is something you can work to mitigate with your CPA.You could choose to form a self-directed IRA and invest the money directly into real estate.  

That will generate a massive tax bill.