@Daniel Kurt - Great to e-meet you and welcome to biggerpockets!  

@E.

It always depends on what kind of investing you want to get involved in and assets you have to work with that are liquid or can be made liquid like a 401k transferred into a self-directed IRA for example.

Utilities - $300 seems fineInsurance - $100 - $150 moProperty tax - I'd say 1.25 % would be more accurateMaintenance - I'd allow $500/mo to start a cap fund for when e larger repair is neededInternet - $100 mo is what most pay for a good bandwidth.

Great, my favorite state just keeps getting better....

Can anyone recommend the best e-sign lease document for Massachusetts?

My favorite way to help lead to this conclusion is to request real and detailed feedback from agents or buyers who have viewed the property.

Read a little and educate your self on some of the terms and investment strategies and then "GO"  My favorite strategy and the most that I help my investors with is the BRRRR method.

My favorite inspectors do about 4, sometimes 5 inspections per day - thats well over a 1,000  year...How do you find a great inspector?

STR will still offer rental income and you will hopefully have a good CPA who will structure your schedule E correctly for standard deductions and showing a positive net rental.