@Will Crayger, glad you are interested in real estate and a part of the BiggerPockets community.

There is a shoreline and a ridge line within about 2 miles of each other.

I have some capital, and a lot of motivation to grow my company.

I started out with the intent to flip, but after more investigation on taxes and a little unsure of which direction to go.

In fact, I am too afraid to start, but I would like to get going and jump on the train of real estate.A Little about me, I have a BS degree in Mechanical Engineering and a masters in Engineering Management.

One bathroom just needs work and a new toilet, the other needs to be completely replaced. 

You need to ask your local county tax office if a transfer fee/recording fee applies in your circumstances and, if so, how much you will have to pay.If your question is really asking whether there is an income tax consequence of transferring real property title between an individual and a corporate entify, or from a corporate entity to an individual, the answer is maybe.   

The ability to walk away is key and a 1031 in most cases (not all) hinders that.  1031s have a place, but they are not the end all be all that some would like to claim.        

I have a rental property in Connecticut with one insurer, my primary residency with another insurer, and a short-term rental property with another insurer.

In most cases they will help you with screening and a host of benefits for a LL.