You can avoid probate with a "living" trust and still get stepped up basis, but remember attorneys don't know taxes so hire a good tax professional.  

Break the task apart and hire the inspection.

If I am planning to do some of the work myself and hire subs for the remainder, how to I present an acceptable rehab proposal to the lender?

I plan to hire out the plumbing and electrical and do the painting, tiling and flooring myself.  

You're sending your drawings and tech requirements to a manufacturer in China, they make a house for you, ship it to your location, you hire a crew to assemble that house in your place.

We also "hired" someone to fill the role of "property manager" for a few bucks a month (we never even knew that term).

Basically every expense line item on your analysis spreadsheet will be filled out based on the market/property This might take days or even weeks to do depending on your level of familiarity with the market, submarket and property and the responsiveness of the seller/seller's rep  Level 3: the "time to verify" analysis  After you get it under contract you move to Level 3 where you verify your assumptions during due diligenceYou verify all the line items in your analysis spreadsheet by looking at leases, water bills, bank statements, etc. 

I'm probably going to hire a lawyer since I live in MA, the most joyous of all tenant friendly states.

If you fix a light socket wrong and the house burns down you might be held liable, but if you hire an electrician they could go after LLC but not you personally This is why I use multiple LLCs and own little in my own name.  

If you feel like you might not be respected because this is your first and you are young, then hire a property manager for couple years.