Most of the vetting and signing up can easily be done through email and using website.

This service is provided by several authorized 3rd party companies.2024 update: If you file more than 10 1099s, you MUST eFile them now.Here are some of the online 1099 filing companies, and you can easily find others:tax1099.comWageFiling.com1099online.comThese companies charge under $5 per form.

I am not so much worried about this year but thinking about how easily I could sell a potential property in 10-20 years. 

After that, they have returned 2 more times and I assume they are going to do their best to be allowed to get in the property.

While this would not necessarily result in immediate taxes (because it can be offset by your lifetime gift and estate tax exclusion), a gift tax return (Form 709) would need to be filed.

You could put in a range of numbers for purchase price and closing costs, renovation expenses, and expected returns and you could very quickly get a range of projected return on investments (although an excel spreadsheet could easily do this as well), but I'm sure as technology develops we will see even more sophistication in AI's ability to assist in deal analyzing.

You need to understand how to drive the Net Operating Income to produce a good solid return. 

Many of which are savvy BP type clients who are doing updates/raising rents and then the buildings do cashflow positive even with lower down payments which produce amazing returns (at 3.5-5% down you get close to a 50%+ return a year just off mortgage paydown). 

And, even if he has real estate clients, doing a tax return doesn't really educate one.

When filing the LLC return, it is important to ensure that these liabilities are accurately reflected on the balance sheet.However, it's essential to note that distributing the refinance proceeds among LLC members could potentially be viewed as a taxable event if there is no intent to repay these amounts to the LLC.