I will just have my bookkeeper bill a flat amount monthly from Jan 1st on. 

Flat Fee buyer agency to reduce acquisition costs (get ~2% of the sales price back), and flat fee MLS listing to reduce selling costs to ~$500.

I am just looking for insight from local MA realtors, attorneys or landlords regarding what my typical monthly expenses (if any) will likely be (I don’t mean one-off expenses like roof repairs). 

I came across a 2-flat with a basement that has been converted into garden unit with 3 bedrooms and kitchen and bath.

The excitement then went through the roof and the owner wanted to do three or four at the same time and the next thing you know the whole ship went down in bankrupt.Just something to think about. 

I do have a nightly pet fee but i put in my listing that if someone is bringing a pet for an extended period of time they can also reach out to me to discuss a flat pet rate for their stay.

It had some deferred maintenance and I put a new roof on and fixed a few things.

Actually, a friend once mentioned a unit in Eugene that had to be re-leased after a nasty storm tore off part of the roof.. it’s gritty, hands-on stuff like that which rounds out your perspective.At the end of the day, you don’t need a flawless blueprint to get started.

Let’s say just a roof repair and a little bit of dry wall and paint and replacing some door jams and baseboards.

Also the value (in this case) is determined by the NOI, so assuming it will be worth 2x, is assuming your NOI is thru the roof (which is can be, but it's not likely in the first 5 years).