Most paid way too much, based on multiples that were based on weird years. 

I am running numbers based on the worst-case scenario. 

Also discuss with the contractor the time expected for the project if its small, mid or large and if it needs permits and how long would it take for permitting and all, also payment terms, make sure you go with payment terms that are fair to you and the contractor (so many terms but most common is monthly based on completed work with an upfront for materials) and ALWAYS keep the last payment until project is closed (retainage) and you do your walkthrough and if there's any issues you write them down and provide the contractor with (punch list to release the retainer once they're corrected or fixed). read about how to deal with contractors and always ask for references but it really depends on how big the job is, personally I wouldn't spend too much time doing due diligence on small jobs such as door latches or shelving rather on additions, layout change and other scopes.Good luck!

My biggest fear is getting on the phone with a potential seller and not being able to articulate or persuade them to sign a contract with me.

Meaning, we can't over-improve a property based on the neighborhood. 

I would be happy to talk to you over the phone on what I have learned as well.

They also sometimes have a phone number for neighbors to turn violators in too. 

Then, run your numbers on the potential STR income - what are your expenses going to be (they will be more), and what is your projected income based on looking at competition in your area on the sites?

I  am happy to reach out and provide my phone number or Facebook orcoach.I owe 10 grand on the 2 bed I forgot. 

Since it's in a trust, you might not get accurate phone numbers, but you could still try skip-tracing the address and attempting the numbers it provides. https://batchskiptracing.com/