When it comes to any planning for any kind of operation, we have to effectively identify risk.

Your letter may have the effect of driving out your tenant if there is no viable alternative. 

When California put into effect the Shelter-in-Place, I brainstormed how I can bring more value to our current situation.

Canandaigua as well as other portions of the Western NY area, are great for investments, as long as you take the tax liability into the equation, as well as new state laws that took effect last year, that need to be accounted for, so you go into any transaction eyes wide open, and all (realistic) numbers in the equation.

In exchange it is possible to get a reduction in rent for those who are able to effectively self manage the property, as well as additional opportunities to make hourly wages as high as $21 an hour.

@Robert HetrickPer the loan offset rules that went into effect with the 2018 Tax and Job Act: if you leave your job and the loan is current at the time you leave your job but then the loan goes into default because you left your job, you will have until your tax return deadline (including any timely filed extension) to make the loan current by depositing the outstanding balance into an IRA (and thereby avoid the taxes and penalties that would otherwise apply).

You need a calm consistent demeanor and the ability to handle and solve problems and you have to effectively deal with lots of different personalities.

Upside to raise rents to $2,500/unit in Year 1 (but I'm trying to be conservative in my numbers for this exercise).

From a gut feeling, it feels like there are a much higher amount of people just waiting for "the next crash" as if it's something that's guaranteed to happen.If this is true, then wouldn't that soften or even negate the effects of any downturn that may occur?

But in effect they're the same and yes it's common.Generally the only way to avoid points or an origination fee is 1) going directly to the lender (no broker/intermediary involved), and 2) have an established relationship with the lender. #2 could mean either that it's a HML you've done several successful deals with, who cuts you a break and eliminates the points, or is a private lender who isn't real estate savvy and doesn't even realize points are common.It's basically the same with lending as it is with buying houses: The more work you personally put in to make the deal happen, the better deal you'll get.