Landlords issuing 1099s is a grey area.There is no strict requirement for landlords to issue 1099s, and I have never heard of the IRS going after landlords for failure to file 1099s.That being said it does not necessarily mean that 1099ing your contractors is a bad idea.And remember the 1099 threshold for something like mowing lawns is $600 for the year per recipient.

So it's usually the second month and going forward when you'll receive your proceeds.You also mentioned that the tenant is a housing voucher recipient.

So my newest question to those of you who have experience with direct mail campaigns on the site "Realeflow" is this, under a few of the recipients names (for those who I am sending post cards too) are LLC'S.

As far as you paying income or cap gains, if it's classified as a gift, the recipient never pays taxes unless the donor would be required to pay and doesnt.

For disputed ACH payments, the receiving bank is obliged to investigate and consider evidence presented by the recipient (the landlord).I anticipated this problem and therefore never use Cozy for rent collection.

Some payments do not have to be reported on Form 1099-MISC, although they may be taxable to the recipient.

I have done some research into the situation and it appears that the local housing authority has strict rules for the recipients of their services. 

The more the advice is tailored to the recipient, the more likely it will be viewed as a recommendation.

If they gift the property, the recipient takes a "carry over" basis meaning they also get the parents' basis. 

I plan on fixing it up a bit and selling so i can have enough capital to buy a small multi-family.I've read that if the recipient of the "gift" sells the property quickly then he/she will be taxed significantly more.