I am selling a property to a buy and hold investor and accepted a reduced price for a "time is of the essence" quick closing.

You are reducing your taxable income by $119 per month.

As such, again they will beat out a pre investor 100% of the time and for what they are doing (basically locking in a place to live at a reduced rate) its rational.

Look into CPA's that are able to reduce costs by working virtually with you.

Let's assume I'm smart and lucky enough to buy something with an opportunity to add value without a lot of out of pocket cash (reduce expenses and manage it better, for the sake of argument) and 12 months from now it's normalized and worth $1.3 Million.

The property financials the seller provided show big cashflow but I noticed he has no debt on it.I would have to mortgage the property which could end up reducing cashflow down to around $100/door.

My brothers and I don't have an agent because we wanted to reduce any expenses (i.e. agent commission) we could since we are just starting out.

Just a method of reducing vacancy from the start and driving traffic just slightly with a simply modification.

Ask your employer's payroll department how many allowances you can claim to reduce your refund to an acceptable level. 

Me personally i would not fix anything in the house now. it will be a burden for your grandparents that are still living there. plan ahead and have the money and the contacts ready to move in on the house as soon as you can (i also hope its no time soon) but being ready should reduce the downtime for the house. and when the rent starts to come in you can use that to pay of the rest of your loans. let your money make the money you need to pay the loans...