I would ask the seller to present you their previous leases and any kind of documentation they can provide you. 

We've been chatting with insurance brokers and a couple things have come up that I'm not sure about and don't know if they brokers really know either.The property will be owned in the LLC's name.

I was hoping I'd find support for whether or not it would be a good idea to get hard money for a 25% down payment, traditional financing for the remaining 75%, with all profits (rent less both loan payments-HML and traditional financing, prop tax, insurance, and 10% maintenance fund) going to the hard money lender under the loan is paid off. 

If you are 5th in line, you might want to also start looking for some other properties in the meantime.If you  have only a tax certificate, it is sometimes hard to get property insurance.

Master insurance policy issues can be daunting as well.Seems to me that it would be easier to construct a duplex.  

Make sure though that they are licensed and insured to do snow plowing and not just a "chuck in the truck" because there are a lot of those offering plowing services.

I am an Insurance agent by day and real estate investor by night and weekend. 

This will not be considered toward sale price if tenant wants to execute the option.Lease : $2,000 - Fair market rent.Tax and Insurance -- Landlord responsibility.Utilities and Maintenance(Lawn) - Tenant responsibility.I appreciate your time and advice.

The house is free and clear with just taxes, insurance and utilities to be carried until it sells so that is not a major roadblock.

If i get approved for a Maryland Mortgage Program loan that covers 20% of my down payment, will i still have to pay for a private mortgage insurance?