It is not an earth shattering concept but often the foundational items are what make a good/bad decision or deal. 

I don't have a traditional income (just started a digital company with international clients, and most of my equity is based on stocks), so I don't qualify for regular loans.

Also will have large ticket items or Capital Expenditures you will need to set money aside for to make repairs when the come due like the roof, siding, HVAC, and etc..Lastly the turn over process starts it all over again minus the loan and closing cost aspect.

If you have no money right now, I would recommend traditionally purchasing it from your Mom, put a small mortgage on it and get some cash back from the mortgage to keep on hand for reserves.Good luck on your journey and do not let this opportunity pass!

Beyond that, there are a couple of big ticket items like the roof which may need replaced, and the wiring because I'm not sure if it's got aluminum wiring or not. 

Property management is a separate cost, and 10% is usually what I account for that.It has worked for me for properties that don’t need a roof or foundation (ie high capex items) at time of purchase. 

.- Current mortgage balance is $249k, payment (w/escrow) is about $1488, estimated current value is $360-380k- I am software developer, recently switched from W-2 to 1099, which prevents me from getting a traditional mortgage for 2 years.I have been considering selling my house and potentially moving further south where the climate is a little warmer.

What if I couldn't secure the full amount to purchase a property and instead could only come up with 20-40 percent; Could I get a traditional loan with a promissory note along with my W2 and credit info? 

Looking for a contractor who can replace siding with traditional wood look. 

Depending on your goals items like; population growth, job growth, rent growth, job diversification are items that better help you understand a market's growth opportunity.