Hi Igor, on ROI versus cash flow, both items are important but in my opinion positive cash flow is very important on rental units and that seems to be what most buyers are looking for.  

I get an independent opinion on repairs needed versus the locals who know this is my first rodeo. 

Even though you are paying yourself back with interest, the money you borrow isn't working for you in the 401K portfolio while it's out.I used Bankrate to do the 401K loan calc:If you can borrow the money through traditional financing, the rental income will pay that off and your 401K can continue working for you.So, you have to weigh that opportunity cost versus going through the financing route.

If you have 3-6 months saved up and can go ALL in, wouldn't this be better energy output versus part timing it?

There is also a difference between her wanting to learn versus you wanting to teach her....the first usually has to precede the latter.

New agents often overvalue themselves because they want to believe in the dream versus the very hard reality of what it will take for them to be successful.

Really it comes down to what interests you, resources, model, risk tolerance, neighborhood, and degrees of active versus passive.

Isn't it better under an LLC versus doing it under your yourself?

I would honor the deceased wishes and use Agent #1 personally, or hire a discount broker who will list for 1% or a flat fee.Goodluck...I do not have listing versus actual, but DOM were good.

While a suitor may have an interest in finding a judgment against you that results in them taking over your mansion, their interest is likely to be higher when they acquire it free and clear versus owing a large monthly payment against it.