Right now I have a sole proprietor LLC, and a home based office.

I am going to assume you don't declare that income to the IRS on your tax return and pay the proper amount of taxes on it.If it is not on your last two years of tax returns,you will get no credit for it from the traditional banks and lenders which means you ability to borrow money will be based solely on what little you do declare and have taxed properly.Your savings and checking account s and stock holdings are irrelevant,only your verifiable monthly and yearly income.Your only choice would be a hard money lender at an enormous interest rate.

Not sure any cons with exception the value is based on appraisal and not how the asset performs.

Mortgage on $375K based on 4% for 30 years is $1,790Total Yearly Expense is $29,410 and Monthly expense + Mortgage is $4,241The property is giving income of $5200 a month from all 4 apartments, with monthly Cash flow of under $1,000 a month.Even that Cash flow look very good, the Cap Rate is only 6.28% and COC of 7.67%.Also owner is offering to "hold mortgage for balance" - what does that means?

Based on number 2, I schedule them for the next round where I meet them in person at one of the properties. 

You are correct re: last 5 to 10 years but all locations have cycles and helpful to understand where in the cycle you are and just understand that if you believe you are in the later innings based on historical averages of the complete cycle does it make sense to jump in or not or find better markets in different parts of the cycle.  

I guess based on your answer for #2 that they will go off what the agent says is physically in the comparable property in the MLS, since they can't actually get in there to inspect it.  

Paint companies put together their popular colors or what they forecast for that year as trending in fashion and based on "Region" but there is a reason the chip wall and fan decks are so all encompassing.

I am basically employing contractors that find leads on a commission based compensation.

New York City-based real estate investor building a high-performance portfolio of investments in Northeast Ohio where I grew up.