While yours would not have the mortgage payment to make, a good leveraged deal will generally out perform a cash deal.Second, you will have to save up an equal or greater sum for your next property.

If I am following this you have a current mortgage that you wish to pay of with a hard money loan before securing a new mortgage to pay off the hard money loan.

If you bring me one I will allow you to shadow me through the process of acquisition rehab and sale / and or securing permanent financing.4) Don't know much about lynn.

You need to consult with your attorney and them draw up an operating agreement that spells out each of your roles, duties and responsibilities as well as consequences for not performing, and how the company is to be dissolved if it ever needs to be.

If the deal performs well I could care less if anything is available online; if it does not perform, having access to past history makes no difference as I have that history anyway.

I would recommend giving 3 VA's the same task and see which one performs best and determine which will be the best fit. 

The only "technology" I might consider offering is a security system if a tenant really felt unsafe, though they can easily get their own.

A "deed of trust" is a security instrument. 

I have a lot of friends still in the area and a great property manager that only charges 7%, so it feels secure. 

I know you mentioned potentially a larger security deposit or paying six months rent upfront, but I have a feeling holding her to different standards than other tenants might cause you some issues based on information I have studied (I haven't finished the course for my real estate license yet and I'm no expert or attorney), but better safe than sorry!