He started out doing some snow shoveling and plowing for me and then some mowing when I was out of town and now he is my right hand man.

.- Make sure to dish out any maintenance for yard work / shoveling.

You’re shoveling snow with a shovel; they are using a snow plow.  

So after talking to her a bit more, I came to find out that the reason she wanted to move out of the house she renting is because she did not read her lease thoroughly before she moved in and found out that she had to mow the lawn (and supply her own mower), shovel the snow and pay a service fee anytime a service man had to go to her house to fix something. 

I would use the minimum I needed to make the STR successful, and have a backup plan if the STR lost money.In other words, this might be best suited for someone with a big W2 shovel, they just don't have the full downpayment built up yet, but if they ran into future issues or slow STR months, their W2 could cover it (and the HELOC payment).Also, you have to really research your STR investment first to be almost certain it will profit.  

Then send up the flare warning others. 

It's only 3.5% down + closing costs and reserves.Work your day job, mow lawns, leaf cleanup, shovel snow, flip furniture, pick up night shifts waiting tables/bartending, stock shelves at home depot overnight if you hate talking to people or anything else.

Shovel snow and do grass ant little stuff like the boiler for a discount?  

I try to identify a good tenant who might be interested in a small discount for taking care of cleaning and shoveling snow.

Granted, this can be a learning experience about how to harden rentals properly, but it often creates all kinds of nostalgic sentiments that can flare up into conflicts with the tenants.The usual scenario is that the tenants move in, live as tenants do, and the newbie landlords go back in and find delicate stuff, or meaningful stuff, or stuff that they didn't even know was meaningful to them damaged or painted over or disrespected in some way, and then the newbie landlords get in this forum and moan about how tenants just don't respect their landlord's property, and they get ten other newbies commiserating and telling them that yes, yes, yes, they're right, and their tenants are bad, bad, bad...and of course this can lead to all kinds of poor decisions.