If you think hiring a CPA to discuss your plan, how you can do it, and all the roads you can take with that, than that is the best option for you!

Later I asked for a list of repairs for clarification and she didn't recall anything about the driveway at all and said "Oh I was probably talking about the road work that was going on".

You can kick the can down the road only so long, at some point capex exceeds cash flow.Also, stay away from weird properties.

It will be money well spent.Also, criminals know how to check which properties in the area are STRs and might be vacant during most of the winter.  

Also, was there a background check on the tenants possibly having criminal backgrounds and or background check to determine if the tenants had ever been evicted in the past?

Likely it is just a quit claim deed to your new name, however, also note that some states (ie MI - requires another form to be filled out and it changes our taxes - or can change them....).Get the help you need to make sure it is done right without costing you extra down the road.  

Cruz seems to focus more on seller financing which seems to be limited as a lot of sellers don’t offer this.  90 day rental road map focuses on private funding with exclusive lenders for their students that will fund 100 percent of the deals.  

Storm sewer, storm pond, sewer lines, water access, fire hydrants, public bathrooms, surface coverage, sidewalk or bike paths, setbacks, power lines and right of ways known and unknown, road access, etc.              5.  

A well-documented plan should help you avoid project changes down the road, but if the inevitable happens, there should be a process for handling the change.

Meaning if you only 'pay in' on say 50% of your income each year by using the S-Corp strategy that you will also only get a proportionate retirement benefit down the road?