Its a very hit and miss area in terms of crime. 

In terms of liability - I'd recommend at least a million.

In terms of learning about the different markets it's simple but it takes time.

I am curious to know the difference between an 'Investor Friendly Agent' and a 'Regular Agent', in terms of:1.

@Amanda Forde I have two rentals in Dorchester and while I had expressed the desire to raise rents last year with the tenants, both have been great in terms of taking care of the units, and being respectful neighbors, and of course paying on time.

My options are open in terms of my next move.

In terms of learning about the different markets it's simple but it takes time.

(in terms of creating a sense of urgency and competition for completing the application, you could even fill out some fake applications and create your own stack, although I am not sure of the legalities of doing so). 

Since my post, my client was buying full-priced higher-end homes, all on one street, and I was able to pre-lease using live videos and virtual tours, set the market rate, higher than the surrounding homes, help him get it made ready, any new additions, shared my resources in terms of contractors, get him everything he asked; copies of leases, deposits, etc.

I am just not sure on how to proceed in terms of my first rental property purchase.