The few investors that I know that execute the strategy well are basically magicians, or at least have amazing project management skills, experience dealing with contractors, and loads of free time.

I would venture to guess that you bringing an estimate from a contractor saying the work will cost less than $100k would have NO impact (at best) and a negative impact (more likely) because, back to the original point:  the discomfort may well be with you and your ability to excellently execute this complex deal. 

This person can then help you actually execute the deal while teaching you along the way:Look your deal over from top to bottom and determine if you have a "deal" (run the numbers, do local market due diligence, property due diligence, etc.)Conduct and-or participate in the negotiations  Assist with the team building process (property management selection is absolutely KEY)Create deal package/loan request package to help raise the equity and the debt (not so easy anymore)Help guide both you and the deal through the acquisitionHelp initiate and execute the business plan, working closely with the property management companyAssist/teach you how to asset manage  You can start looking for that person right here on BP.

We are about 1.5 hours from the border.Airbnb's reduced staff is causing issues and won't get better as think heat up with Summer bookings. 

Everyone works from home now and even when the orders are lifted do you really think the top executives aren't going to start unloading their over-bloated leases in order to downsize and reduce the amount of workspace and bottom-line costs?

The quote for contractor-B only takes about $300 but the staff at title company still gives a $700 check to contractor-B (even after seeing the quote from contractor-B of only $300).

I have $20K saved and I am primarily interested flipping houses/executing brrrr deals in or around the Lehigh Valley.

@Cayman Fox Take the time to educate yourself on the real estate business as a whole so when the time comes when you have the money to execute you hit the ground running in terms of a strategy. 

Get everything lined up before the deal as best as you can so you can execute when you find it

Don't question it and execute and take action.Good luck finding the right fit for you!