There are no tax deductions for such gifts, however you have a $15k per recipient annual gift limit that avoids the chore of filing a gift tax return.

I would recommend matching old reservation rates and offering free gifts to secure good reviews and booking momentum. 

  $500 off up front is a one time discount, the $40/month lower is the gift (to the tenant) that keeps on giving. 

They keep rent low, give gifts and homemade cookies for Christmas, make upgrades whenever the tenant requests,  accept all the late rent excuses, etc.The truth is, your tenant is not your friend.

Don't start throwing ideas at them like seller financing or numbers etc until you have an idea of if they actually intend to sell and what their needs are around the sale.

In a total package deal for a single family or multi what do you look for? Does price per square ft factor or is it just ARV. What percentage ARV do you shoot for? If it’s rental property do you seek amenities in the ...

We don't know whether a presidential idea will be implemented at all.

Quote from @Simon Horowitz: I'd love to connect on here with trustworthy contractors that I can bounce ideas off. 

But I certainly am tossing the idea around. 

Would a HELOC or home equity loan on my personal home be a good idea to fund this?