Perplexed that a service provider to whom I'm willing to hand over my business decides to drag their feet. 

Why would you decide to lose the income from the other unit and add on construction cost to add space?

Hi everyone,I'm hopefully purchasing a rental property in Boston (some sort of condo or duplex in Eastie, Dorchester, South Boston, Seaport) soon but am wondering whether I should hire a PM. I've yet to hear anything ...

If you decide to pursue I would offer 3% higher than what your top dollar is in order to pay your agent and still have them do the paperwork so you are protected.

Tenant's guest did significant damage to electrical and tenant has decided to go live with Daddy instead. 

My wife and I started our real estate investing journey around 7 years ago during the real estate down turn when we were unable to sell our first house without loosing money, so we decided to keep it and rent it out. 

Write your offer, through your agent, and let the seller decide what they want to do.

I  recently have decided to switch my business from flipping and small holds, and attempt to buy bigger multifamily and commercial.

I believe for your first investment property you should look into using the Master Lease Option method, it has the least amount of risks as there is no down payment and and you can essentially "test drive" the property before deciding whether or not to buy it.

Ultimately if you don't sell and someone (family, friends, siblings, etc) inherits property, and they decide to sell later, they pay capital gains tax based only on the value of the property as of the date of death.