Rent is due Sept 1, it is odd for tenants to pay well in advance (unless they paid last month's rent with the deposit).4 weeks is enough to find a new place especially if they get started now and as they have one month's rent to use as a deposit for the new place.

You could schedule showings during a time frame you are available and require people to pick those slots.

I have had a number of questions (how to handle land contract payments, how to set up security deposit refunds, etc.) and between their online support and responses to my questions via email, I have yet to run into a situation I couldn't address. 

.- 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 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.

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.

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