If I inherit a tenant who refuses to use digital means I will just have to find a new qualified tenant. 

You can potentially use 75% of the long-term rents to help qualify. 

At first glance though, it looks like investors can go as high as they want (while still qualifying for a loan) and as many times as they want.

If you insist on using a VA loan, it's written in VA guidelines in black/white that only folks re-upping can use their military income as qualifying income within 12 months of EAS. 

Anyone may assume a VA loan as long as they qualify with the lender, but only a veteran can obtain an initial VA loan.

I have a property that has been on the market for over three months now without receiving a qualified tenant and I may want to sell it to get some liquidity.It has also been hard to receive monthly profit for myself since my property management has a portfolio minimum of $2k until they allow me to take home proceeds at the end of the month.

If the property needs substantial repairs or otherwise doesn’t qualify for a mortgage (negative cash flow, vacant, etc.) it may be the only way to get an acceptable offer.  

Telling the truth or directing someone else to tell the truth will never qualify as a negligence.  

Based on this link it seems the IRS still qualifies it under ordinary income.  

A whole cottage industry was spawned by him. 3 day class and you're an expert qualified to handle people's retirement money.