Right now Milwaukee is very appealing to me with lower cost of entry and still easy to drive to.

The ultimate goal in determining whether the provider's account fees meet your needs should be the value provided, not just in fees you'll incur, but also including intangible factors such as highly experienced professionals and responsiveness to client needs.Funding Time Frame - I would argue that this is the most important factor, as moving quickly is the nature of the real estate investment community. 

Your contractors will be the second biggest determining factor in your success (other than buying at the right price). 

Many will say you should still factor in a mgmt fee.

I never liked owning rentals more than a 15 minute drive from my house, so out of state would be a big NO.

Though there will be many factor that underwriting (and any good mortgage banker) will look at - when was the property bought, was it bought as primary and then switched to investment, how long as it been an investment, how far is it from the new property, it is nice then the new property that you want to buy, etc.The point been that the new purchase needs to pass the smell test.

Ideally, I would like the property to be within 1-1:30 hr of driving distance from me, so I'm considering properties in NJ, NY and CT.

As a matter of fact Bigger Pockets (the social media site you & I are currently on) happens to be one of the best social media sites in regards to driving traffic to your website.

We'll see how the second unit does, but it may not cash-flow until interest rates get jacked up and people are forced to rent/drive the rental market up to catch up with the sales prices.Would like to pull equity out and throw it at another property eventually, maybe a HELOC, but won't be able to right now since it's owner-occupied financing with low interest rates and that might raise flags and require me to refi. 

I use google drive, google sheets for accounting, and an amazing app called cam scanner to collect receipts and scan other documents that I can upload into google drive.