We are planning on doing the bathroom and kitchen higher end, as well as keeping everything as close to period as we can so it doesn't loose its charm. 

If it's written in metes and bounds, you may be able to get a fairly good idea where the property lines are from reading and measuring yourself as it will reference landmarks (such as distances from street corners, alleys, etc.) and angles.If you decide to put up the fence the vendor will need a boundary survey.

I know being new to this im bound to have little slip ups but I want to start off strong.

With that in mind, who should I consider "essential" (I use this word loosely) to my team for the FIRST investment?

Estimating ARV is going to get tricky in some markets as prices are bound to start softening.

Cash flow management issues and they need the money now to operate with - BAD NEWS - mostly likely to result in loosing your money, most likely to result in poor project management, scheduling issues, inflated change orders, or just plain walking off your job and leaving you stranded. 

What are my options on increasing the rent/removing tenant that are within the bounds of law? 

Does loosing sleep at night seem worth it? 

@Mark MillichAre you willing to loose what you paid for it?

Make sure you’ve got confirming these things on there or you’re bound to learn this lesson twice.