For those of us in the South, this is a pretty constant problem even in winter time.

@Matthew Haralson, I put together some thoughts on your question that may be helpful to you  at https://www.biggerpockets.com/blog/effectively-conduct-joint-venture-agreements-as-a-real-estate-investor. 

Your last comment about the current tenants saying they now want to stay because they can't find anywhere else tells me 4 things:1 -  they want to leave, and will at the first chance2 - They can't afford the current rent, so you aren't going to be able to raise it...and get it...as in "they will constantly be late, and eventually not at all.3 - They will constantly be late with the current rent amount.4 - The fact that the Section 8 means the rent will be consistent means they will be consistently late...and you will be consistently in the negative because of it.Run away, as fast as you can...and don't look back. 

We have done many joint ventures in the past and continue to do so.  

Through it I've experienced many unforgettable moments that I only imagined prior, a unique sense of our world, constant travel, and friendships across the globe.

This allows a taxpayer to exclude up to $250,000 ($500,000 for certain taxpayers who file a joint return) of the gain from the sale (or exchange) of property owned and used as a principal residence for at least two of the five years before the sale. 

You may need to cut relief joints in the plaster to get the sagging floors to move.

When you combine the houses into the same LLC you can jointly use the funds to fix whatever is most pressing from all the repairs needed with the combined funds. 

You can use constant contact, mailchimp or your crm to let them know of your deal.

The 2019 standard deduction is $24k for married filing jointly, and we generally do not have enough in mortgage interest, charitable contributions, etc. to itemize, although we could work on being more strategic with those things.If we purchase a turn key property or other real estate investement, we would be able to deduct business expenses and depreciation.