Realtors will always tell you you need a realtor - that is their source of income so you can automatically ignore their responses to this post. 

I have to do it annually for my commercial loans with personal guarantees.I would guess it is a boilerplate request, since typically taxes are due April 15, so they automatically reach out to all borrowers that have not already submitted in May. 

So, is it automatically a sign of someone with bad credit?  

It just shifts debt from one to the other.Don't get too extreme in your attempts to save tax just to save tax. 

Now with COVID19, we might be looking at a shifting market.

So can I do an automatic withdrawal from his Social Security for his rent payments?

Even though it’s family, treat it like a traditional business deal...draft and sign a promissory note, record the note as their having the 1st deed to the property so that they can be named as loss payee on the insurance policy, just in case.Also, something to think about on both ends, buying and selling to family, you should pass the commissions that you would be paying to an agent along to any family member who is buying rom you, or vice versa...automatic 6% discount, as that money would have gone out the door anyhow.Best of luck!

Which is wonderful news, because if it was this easy and automate-able, then wall-street would simply buy the top 10 in every market in America perpetually and you and I would have no opportunity.  

There is evidence that generation ally, there is a shift towards experiences over belongings.

Ugh - Since I think the market is shifting towards faster increases in expenses than income (rent), it'd be worth investigating.Don't know the cost, but water submeters are not that expensive to buy (<$200 each) IF you can install them cheaply.Electrical sub-meters, don't know, but I'd do it unless I'm really tight on funds.The idea is that you bill tenants back for their actual usage, which is why flat rate RUBS are kinda dumb.