@Ben Bymaster I feel your pain.

One pratfall on video and difficult-to-disprove claims of shooting pains, with the above email to document that the tenant warned you in advance about the "problem," and you're in trouble.Just look at the email.

It can be a pain because they are very subjective... it depends on what inspector you get.

I have been there in my personal residence and it added a little more pain to the process.

Long term tenants can be a major pain when it comes to increasing the income on a property when renovation is necessary.

We have  had properties all over the state and the preparations and damages are a pain.  

You would have more tenants to deal with, but your risk of losing income is divided between the 3 tenants. i.e. having 1 tenant move out of a 4-plex and losing 1/3 of your income is less painful than having a tenant move out of a duplex you live in and losing all of your income while it is vacant. 

I would do Whatever is the least pain...…. financially NOW.You mentioned it is favourable to hold off as it is winter.

@Michael Joseph Allen IIWell say if you had to evict, it could be a painful process.

Because we are thinking of this as a flip, I would think that traditional mortgage would be a real pain?