Eventually, when we move out (say 3-5 years) and assuming rents rise 5% we could be cash flow positive at about $825/m.

The goal is to eventually move up to multifamily and possibly apartment investing.Hopefully we can find a local REI club in the area to meet up with other investors.

I'm just worried I'm going to wind up spending $20k to do it, but these updates will need to happen eventually. 

If anything, send them a monthly postcard in case they eventually decide to sell your name will be ingrained in their mind.

How do I find Licensed Contractors to interview, get estimates, and eventually hire?

A lot of them will eventually pay because they still need roof over their head.

I focus on 1) making sure they have verifiable monthly income from a stable job that equals 4x monthly rent (gross income) + 2) no history of eviction (at all even 10 yrs ago is a show stopper for me) or recent judgements >$2000 (the concern is that they're going to get garnished eventually). 

My real estate goals are to eventually Buy and Hold as many properties as possible as well as developing .  

When block chain succeeds, crypto as Fiat eventually will too, otherwise there's little incentive for miners to mine.

We have numerous rental properties,  but since  it is a high end home, and eventually our own home  we have reservations.We have to make some decisions on this quickly to define financing and capture the rest of the peak rental season so quick feedback is appreciated.