Account Closed  The market here in eastern MA is suffering from an extreme lack of inventory. 

And for sure it will complicate your bookkeeping and accounting. 

I work full time as a corporate accountant and that most likely won't change anytime soon.

Now if you are doing a monthly profit and loss as part of your underwriting, you do want to account for that.

Looking for a great insurance broker who is experienced in handling house-hack situations.We may short-term-rent our primary-residence unit within SF regulations (up to 90 days a year), which we will also want to account for with insurance (been looking through posts here about some insurance companies cancelling people's homeowner's policies when they hear about STR setups so want to make sure we're above board and with a supportive insurance company).  

Tenants that allow roaches need to be held accountable.

With moderate increases this year, we’ll be at a positive cash flow of over $2,000/month ([$3,500 income - $1,500 mortgage] - Taking into account Cap-X, vacancy, etc. and cash flow is still over $1,500 which meets our goal of $500/door).Fitting that its in the "Milk District", because its certainly a cash cow for us!

It's not like a regular rental, so you will need to have days for cleaning/turnover unless you can afford a service to do it in a couple of hours.The type of home you get will just determine what type of client you'll attract. 1-bedroom condo might attract more business clients traveling solo (some of which stay for weeks and have an expense account), 2-bedroom might get more families on a budget, SFH might get more families more willing to spend.

Get an accountant and for estimated fees. 

Account Closed Well, maybe i'm not using the definition of turn-key correctly - the property was "near" turn-key as a purchase, but I didn't go through a "turn-key service".