Has anyone had to do something like this before?

Expensive markets can be a challenge, but here are deals to be had, depending on the amount of work you are willing to do.

Quote from @Scott Meech: How do I report that ignore user in the forums doesn't work?  

It's a relatively small town and a lot of us run into each other as we do business. 

Do you have a Bank/Lender already that if going to be offering the construction financing or are you paying out of pocket?

Do you have an STR in Plymouth?

I'm not one to take risks but I feel I am capable of becoming a Real Estate Investor as long as I do my due diligence.

Do I need to provide a notice to Tenants that I will be on the property doing maintenance if I do not need to enter any active tenants unit?

It really depends on what the work is that you are doing.. 

Always great to do research and not rush too quickly, but its almost always better when people "make the leap" sooner rather than later like you said, I'd recommend at least putting some pen to paper on a date/deadline to do your first deal versus someday