I use 10 to 15 years for water heater lifespan so $8/month for its cap expense when installed to code using a licensed plumber.Flooring, paint (interior and exterior), appliances, roof, fences/walls, windows, furnace/HVAC, hardscape, siding, foundations, kitchens (cabinets, counters, sinks, etc.) , bathrooms all have lifespans and all add up.

Definitely plan on living there and living it for a while, hoping to increase the value and add some equity to use to get a rental property, and at some point down the line I may end up selling or using as a rental but that's far away from now.

Even with family, I suggest using a third party servicing agent (I'm not a servicing agent so that is not a "plug" I promise). 

Personally, I have 4 rental properties and I just use MS Excel to track expenses and income using a tab for each property. 

After explaining to the rep that the website said to call if I was using a credit card, I was transferred numerous times and eventually sent to a voicemail!

In other words, this would be the main reason for using a broker... maybe you found the wrong  Broker ?

If you are using a lender with decent 203k experience, They should have at least a couple of contractors, since it is the Lender who has to approve your contractor.

Are there any cons to using a long distance RE attorney... besides the obvious not having face-to-face interaction?

You have to get super focused and figure out if your people (your market) are using a specific tool.

Have them recommend a routine maintenance schedule, advice you on existing issues, and give you an idea of what might happen in the future based on the systems you have.On wells, you will essentially follow the same steps but you will be using a plumber.