I do think one issue you should start tackling off the bat is that of financing.  

How did you tackle payroll taxes and similar liabilities ?

@Gregory Jay, whether you decide to tackle a flip or a rental first, you'll need to make sure you have a good team that has strengths that will cover your weaknesses.  

I definitely think bumping up to a 2 bedroom unit will increase value whether we sell in 3 years or 20, especially when combined with the other updates we're tackling. 

The first investment can be the most intimidating but once you get that accomplished it will be easier to tackle number 2.

You should always go with the venture that you feel comfortable to tackle. 

For anyone who has read the book I'm sure you are familiar with Ferriss' proclamation of how great virtual assistants are and how they can practically tackle any job for less $5 an hour.

If you want to tackle it yourself there is lots of information in the BP Free How To Guides.Regarding the down payment, typically investors put as little money down as necessary to still provide the cash flow desired from the property.  

A good plumber could tackle it in a day or two.He'll probably drill into the exterior sheathing and run it into the wall that way and then put a foam jacket around the exposed pipe rather than drill through the slab and sill plate.

I would tackle projects after work and my father, who is retired, would handle projects on my list when he was able.