Current Tenant month month advice?

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Offer accepted on my first house! so excited to be started on the fast lane. As I have been asking multiple question on my deal I am confident it was good, and now the next step would be landlording! I plan on doing everything myself screening, management to get used to it. Anyways one issue is I have a current tenant on the top floor who pays 625 a month. It is 725 but he gives him the garage and knocks off 100 a month if he does lawn work, shovels the driveway etc. I did get copies of his checks for the last year and he has it set up where it is due on the first and late on the 15. He paid on dates of the 6, 8, 10, etc. The lease is month to month so how do I go about approaching him and letting him now how I will run things. The 625 is fine but I am setting it up where it is due on the 1st and late on the 3rd and plan to charge late fee's on the third. He has been there 7 years but I do not want them to get in the habit of paying me 2 weeks into it. What is the best approach for this? thank you!

[Ralph S.]

Congratulations, John.

This is just my 2 cents, here.

Don't start the relationship with your new tenants with a lie. Nuf said.

Second, I agree with Mitch. Bad idea to make the rent one amount, then discount for yard work. IMO, even worse to charge the higher amount and cut a check. Simply make the rent the lower amount and put the yardwork in the agreement as the responsibility of the tenant. Protect yourself, as Raymond pointed out, failure to shovel snow, keep the grass cut, etc. could come back on your, so have a clause that charges the tenant if they fail to keep things up.
The problem with cutting a check, is that the tenant becomes your service provider, or even worse, an employee. You don't want that. Better they just do it as required by the lease.

To be honest, what's the big deal about the rent? A seven year tenant that does the yard work. Count your blessings. I bought a 4 unit, booted one non-payer and was remodeling the vacant unit. The other three "saw the writing on the wall" and all bailed and I found myself with an empty four unit. Tenants get skittish when a new landlord shows up on their door. You don't mention a tenant in the lower floor. If it's vacant, I'd focus on filling that before making waves with the upper.

Good luck.
Ralph