I am a big believer that someone should start by investing in their own backyard, but seeing as MA is very expensive, you may opt for somewhere else. 

My suggestion would be to stick to historically strong neighborhoods - this can be expensive if you want to be near center city, but if you have the budget highly consider - Fitler square, grad hospital, fairmount, olde city.

It has an accounting section where you can log expenses and earnings

In fact it may actually complicate litigation in the event a claim were to arise while adding additional insurance expenses to your real estate operation.To explain why this is the case I’m going to ask one very simple question: In the event a tenant dispute, premises liability, or any other claim were to arise, what prevents the Plaintiff’s attorney from merely listing your wife who it seems is the property deed holder in your fact pattern as a Defendant?

Net income would be the Host Payout of $541.26.But your true net is what's left over after deducting all expenses not accounted for in this calculation, such as utilities, internet, consumables, etc.

So 96,120 gross income lets say 10% expenses (they will add back in depreciation, taxes and insurance) = $7,209 a month x 45% = $3,244 will be your max PITI payment allowedI have a fantastic lender referral, @Sam Sharp, who is also an investor himself. 

You can likely do a higher ltv if DSCR works, but, it will be at an expensive rate.

Manage rental income and expenses using tools like Google Calendar and property management software.

Do you feel that cash flow increases significantly with a trade up such as this to a much more expensive property? 

The choice depends on your threshold of what hassle you are willing to put up with vs what expense is worth it to avoid the hassle.