First Tenant Late Rent Issue

[Charlie Fullerton]

Hello Folks -

Just want to run a situation by everyone here and get some thoughts.   I just bought a multi-family in tenant friendly MA.  One tenant still has not paid September rent.   Spoke to tenant and was told Sept rent should be coming, there was loss of child support, and rent payments will be back on track for Oct 1st.    Tenant has also applied for rental assistance and has a hearing date coming.   This lease is month-to-month (TAW) so I can simply terminate that lease for Nov 1st.   But not sure if tenant would resist and force a prolonged eviction process.   Also not sure if that is wise given the winter months are around the corner which are not ideal for trying to rent an apartment.  

I do not intend to accept rental assistance.   None of the other units are on rental assistance.   My objective is to move the building in the other direction with improvements and rent increases to get higher quality tenants.    So ultimately I want this tenant out.    

This is my first experience dealing with a non-paying tenant and I wonder what strategy I should pursue.

1.   Because winter months are coming, be flexible, collect as much rent as I can through January, then terminate the lease.   

2.  Proceed immediately with termination of month-to-month lease, out by Nov 1st.   See if tenant cooperates.  

3 . Proceed with immediate notice to vacate for late rent to try and force rent payment, and then ride out as #1 above.

4.  Try the cash for keys route in conjunction with #2 above if necessary.   

Obviously I am looking for the quickest and cheapest way to get this done.   I have no idea what type of tenant this is yet.   I don't know how cooperative they will be.   Financially it would be good not to have to deal with this until after the New Year, but I realize I am kicking the can down the road and there are no guarantees how much rent I would get between now and then.   It may be best to bite the bullet, begin the process immediately, and be prepared to have an vacant apartment through the new year at least.   I could do some updates during that time and raise the rent.    On the other hand, if the tenant does deliver the rent and we can get through the winter, then I would be in a better position from the financial and rental demand standpoints.   Unfortunately, I just got the building and have not had a chance to get all my policies / procedures / forms /etc. into operation.    I didn't learn about this situation until closing.   

Any advice, based on your experience is appreciated.  

Also can I legally tell tenant that I won't be accepting rental assistance?   I know you can't tell an applicant that, but can you tell an existing tenant that or is that discrimination as well?  

My instinct tells me to just get it over with, terminate the lease (#2 above) and be prepared for the worst if tenant resists.   

Regards, Charlie