You will develop the reputation of someone who doesn't close on deals which is the worst thing to be in the acquisition world.  

You do not have an expense for management (I assume you are self managing)  Also you do not have electric, water, or gas bills factored in. 

The owner is a great guy who is an investor and developer himself who is great to work with if you have your ducks in a row. 

I'm still enrolled in school so my loans are "deferred" until I graduate and my naive self hadnt realized the benefit paying on them while enrolled until now. 

You will make a lot of friends here as a Contractor, everyone is always looking for someone with the experience, self included.

I have a spreadsheet to track how much I accrue/set aside each month based on the rents I expect to have coming in.My banks let me have these accounts for free with some nominal minimum balance requirements.I have separate accounts for:Working Capital (main account, rents come in, mortgages go out)CapexRep/Maint/VacancyTax/InsuranceCashflowTenant deposits (for self managed properties)https://www.amazon.com/Profit-First-Transform-Cash...

Would love to get some opinions on self managing vs. hiring a PM, specifically in the Boston area.

Our first goal is to develop enough passive income to replace our own mortgage payments and then see where this takes us from there. 

I would develop a solid criteria for size and product type you are looking for.

- Do you have anyone to help you develop the scope of work for the rehab?