Really worried about the current NY market especially rentals, any prospect that rents would improve some time soon? 

Our goal is to use around 2/3 of that for a rental down payment, and a third for repairs and improvements. 

Living at the property will allow you to learn the most, your acquisition costs will be more attractive, and by properly maintaining the home you'll in a small way be improving your community. 

@Robin Krieb I highly recommend Never Split the Difference it is a must read if you are looking to improve your communication skills.  

For $5k to get the property rent ready, it seems like there is very little room for improvements.

Use your time on station to self educate, improve the property, and build relationships with property management companies.

I am specifically looking for a tool to automate maintaining the agreements in the lease and communications with tenants, as well as a ticketing system for maintenance requests, maybe a capitol improvement request functionality.In my wildest dreams I would find a consultant someone local to central Massachusetts who would come in and see how the portfolio is currently being managed and make recommendations on accounting and property management systems and processes for our team to evolve.

Now, as the internet only improves with developments such as Starlink, where anyone with a laptop will be able to connect to the internet worldwide.

Before looking to invest cash in another rental property it might be worth analyzing what improvements to your current property will do in terms of higher rent. 

The standard printed exception as to discrepancies, conflicts, shortages in area orboundary lines, encroachments or protrusions, or overlapping improvements:(i) will not be amended or deleted from the title policy; or(ii) will be amended to read, "shortages in area" at the expense of Buyer Seller.Why would I choose (i)?