It seems that their general consensus on real estate investing is to buy distressed properties, rehab and flip them, only holding and leasing them in some cases (I do plan on purchasing only distressed properties, unless an amazing turnkey opportunity presents itself) The way I see it is, in the short term, flipping is going to make you money a lot quicker, but, being so young and acquiring numerous property's at a young age, holding/renting and having them paid off by the time I turn 36-38 (if the plan doesn't deviate too much) is going to allow for a huge cash flow, help me to build my portfolio even greater and allow me to invest heavily in commercial real estate.

The other friend and I have minimal savings, but we have been studying real estate investing and determined that the friend with savings would help all of us reach our goals quicker.

I could have cash flowed a little more on another 30 year mortgage, but I figured the quicker I get to paying the property off the better. 

Occasionally landlords will pay our fee or a portion if the project is new development or they're looking to get a lease signed quicker.

Owner is wanting to get rid of them all at once with the idea that it will be quicker and easier.

Need to look at the depreciation, the tenant has a faster schedule than an owner, look there as to who can write off expenses quicker and negotiate from there. 

If you have a quality replacement in the on-deck circle, you might decide quicker about whether to fire the current one. 

The longer you are in the game, the larger your network will be and the quicker you will be able to find deals.

I have no idea what the contractors cost is for a mound, so I hope I'm not expecting too much help without insulting him.That would pretty much pay for it, without completely draining the 5k reserve. (10k from bank plus the 4k from the roof)That would be a lot quicker that asking them to do it.

Hope you find a good resolution!