Hey they basically are underwriting the properties based on the 75% of the potential (I believe) or rental income that the property produces.

If you put these saving towards ASSETS that produce income like Cash Flowing Real Estate you can use this cashflow to pay off you liabilities. 

After a couple of years the property had appreciated enough in value that he sold it and rolled the profits into a larger 8-plex which produced a greater amount of cash flow each month, but still not anything spectacular.  

I want to start investing to produce both cash flow as my current monthly income is low and build cash to pay off my mortgage.

On the opposite end of the spectrum, towards the cape (Wareham, specifically) have two rentals purchased sub $100,000.00 with limited repairs (<10k) both producing subsidized rent of $1,800/unit.

Looking to start with fix and flips, then gradually moving into a deal or two each year in multi family units to start producing some small cash flow each month, as well as building equity in the properties to then sell off and look for bigger projects like commercial real estate/apartments in the future.

to ari. i been doing research online, but i have not met anyone for straight questions. my first concern would be paying monthly fees or rent of desk/ marketing/ etc and not producing income to cover them.  

You can not expect to manage their money problems.It will take a while to train them to be responsible as they have never had to do that and you will have to evict a few but in the end a more efficiently operated business will produce higher returns with less work.During the training you must strictly inforce late payments from the get go and set them at the maximum you are allowed in your state.

Is it a strategy to sell your property, and then do a 1031 exchange into a larger income producing property, take out another loan to cover the additional cost and therefore provide you with a new depreciation write-off as well as more mortgage interest to write off right off the bat?

That way you recoup most if not all of your initial costs and you still have income producing land and income-producing pole barns that you could rent out.