I am totally fine with decreasing my lifestyle and being heavy liquid.

Shoot, even just witnessing what an expensive vehicle can do to your net worth every month is worth the exercise. 

One of them was struck by some heavy machinery and created about a one inch wide crack along the entire height of the wall.

Here in South FL, garages are very rarely used to park vehicles.

The wholesaler gave it an ARV of 275 but I feel all wholesalers tend to be a bit heavy on the ARV price to make the numbers look good. 

Would love to get seasoned investors' advice on how they would solve this investment/tax challenge: I am about to transfer 300k from a retirement vehicle so that I can use the money to retire early.

The quality of tenant for single family in that price range may increase, but cash flow will suffer.Instead- I would up your price range to the 150K-200K range and you will find that there are still some deals out there in the major markets that don't require heavy duty marketing or a PM who has insider knowledge.

This is a wayyyyyy heavy appreciation market as opposed to cash flow.

Often a line of credit is not the best vehicle as nose bleed rates that non-owner occupied LOC command. 

Multiple, billion dollar companies are investing heavy in our area, such as Intel, Google, and Amazon.