Hi Everyone,     I am aware Colorado law prevents landlords from charging the tenant's security deposit for the time the landlord spends on repairs (though they can charge materials).

But if you had a deposit you'd take better care because you want your deposit back.

Being 1.5hrs of NYC gives you a lot of options, even Long Island (which typically has more options for public commute into NYC).Give me a shout if you'd like to chat more, I have a handful of case studies on my site as well from deals I've closed/brokered that match the househacking criteria you're aiming for. 

Banks and credit unions are having to offer very high cd's etc. to get deposits in the banks.

If you still need help, feel free to try BiggerPocket's Lender Match tool (currently in beta). 

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.

I have ample credit history (and the score to match).

.- 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.