It is not the ability to pay but for some reason he just doesn't make it a priority and always a day before the grace period or two days after. 

Various news articles indicated that these companies had been involved in alleged real estate fraud.2.A U.S. bank reported that a real estate investment company located in the eastern part of the United States made multiple cash deposits within a five-week period in amounts that totaled almost one million dollars.

I have had that happen....not sure how MA is but in Indy they hold rent they get evicted for breach of contract period.

Others have covered it above, but definitely get a copy of the lease during inspection period. 

Definitely give yourself a buffer period before locking into a longer term lease to see how the "retraining" goes. 

Specifically when you could have used that same money 3-4 times during that same 10 year period building and selling condos.

Do you have to be a salesman for a period of time before you can be a broker in the state of Iowa?  

I would much rather lose $1000 up front rather than a $100 a month for as long as I own the property You don't lose your EMD whilst in the due diligence period.

i've had sellers agents ask that i sign a confidentiality agreement (stating that i won't share the data with anyone except partner lender). when i was getting started and calling on mls properties, i found the agents open to sending me the tax returns. how else am i supposed to figure out what price to pay if i'm not familiar with the market. also for commercial properties tehre is usually a due diligence period where the buyer can cancel the contract. that is when the seller would show you copies of the leases. 

I can make 10 offers in the same time as I can inspect one property in person.That's what the 7-10 day inspection period is for.