I see this all over Philadelphia with Properties built around that same time that are deteriorating due to contractors missing these small ticket items. 

Sorry, I miss read the post.

Am I missing something or is long term rental the better option here?

Skimming through here so pls excuse if I missed that part

I want to make sure Im prepared with the correct documentation to rent out my condo and would appreciate all opinions if im missing anything: - I have the rental application- I have my rental property agreement that I will have the renter sign and make copies of and provide them a copy.- I have the statement of condition that I will have the renter sign and make copies of and provide them a copy.- I will have them provide a copy of their tenants insurance for my records. - Will provide receipt for first and last months rent.- 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?

This approach allows you to capture the missed depreciation without needing to amend prior years’ returns.

I miss it every day. 

If the original PSA is expired without a mutually signed extension betweeen you and the seller you probably have little recourse unless I am missing something.

Which if youve done flips , but not commerical multi before, you wont miss much,  however a 6 fam is a commerical code permit so there are slight variations between the residential code for essentially all trades which if you dont have a detailed plan and you dont double check every code before you do anything but rely on cheap labor to do your due diliegence for you, what could go wrong ? 

Miss by a day and you are paying a hefty tax bill (income taxes plus early withdraw penalty if you are younger than 59.5 years old).