I think that's a big reason why first time flippers often loose money on their first flips.

I know you said you're willing to sit on it but you also have to look at how much you'll loose out in investments if you sit on it another 10 years.

They are not going to take into consideration the cost of what you are providing so you will loose on this deal.You can have a clause to water the grass, but are you going to drive by and enforce that are actually doing it?

Can we simply add him onto my account as joint holder in order for him to have proof of funds to close A.S.A.P and not run the risk of loosing the property?

@Gaurav Mehta in general, the cities in bay area are loosing up the rule for ADU. 

Getting a letter from you reminding them of the day they stand to loose their home is not going to increase their motivation to sell to you.What might help is for you to let them know that selling their home to you is easy.

You are entitled to hold one such insured mortgage at a time - if you move from that property and wish to buy a new home with a high-ratio mortgage, you are required to bring your first property to an LTV of 80%.That said, there are folks who intentionally, or through the loose diligence of underwriters, manage to get more than one 95% LTV mortgage.  

One thing to note when looking at the individual markets, you can make or loose money in any market.

It's like a blackhole - once it's starts it's nearly impossible for these places to reverse the trends - a few places in KS have gotten better - Dodge City, Garden City, Hays - they hang on and are relatively "progressive" (I use that term loosely) compared to their other rural neighboring cities) and have found a way to survive and somewhat thrive in today's society.  

Would it just be better to do a cash out refinance for my equity instead of using a HELOC so I’m not loosing 6% on every house I buy until I can refinance out of that loan?