.- Im thinking of not charging security deposit because of all the strict MA laws and just using the last months rent as a sort of security deposit, thoughts?

If there are large deposits the underwriter will ask for a signed letter of explanation from the borrower along with supporting documents.

Most lenders are fine with just seeing a signed lease and receipt of the first month's rent with security deposit, so the tenant doesn't need to actually be moved in yet. or 80% though it will certainly make the process smoother if you have a tenant lined up.

@Conrado BalicustoWe utilize RentecDirect.com as a tenant facing portal to collect our rent, deposit it to our bank account, market our properties, screen our tenants, handle our accounting and more.  

I win in court and tenant is kicked out in 24-48 hours.In 90% of all situations, the tenant leaves before I have to file in court, I use their deposit to cover unpaid rent and as much cleaning/repairs as possible, and I move on.

I use it, though I hate it, but I avoid problems by setting criteria such as how much in advance a party has to book, minimum number of nights, requiring either a large deposit or purchase of insurance, house rules & photo id requirements prior to arrival, withholding check-in information until just before arrival and sending it to a verified cell phone number.

This allows you to deposit the rent and pay expenses out of a business account instead of a personal account.

Never skip your due diligence OR I would charge the biggest deposit allowed in you state. 

@Vivek Kumar, For a tenant like that I might charge 2 months deposit (max allowed in my state).

I do not take the listing down until I receive the security deposit.