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?

Interesting article published today. https://www.foxbusiness.com/features/10-cities-in-...To make the list, cities had to have rates of negative equity in excess of 8.2 percent, which is the current the U.S. national average rate of homes “underwater.” combined with the city’s mortgage delinquency rate from Zillow’s February 2019 index.

@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.

Of course, the eventual plan is to refinance the home as soon as possible through a traditional mortgage, to reduce the excessive amount of costs with high interest rates from hml.

But shoveling all their excess cashflow into software by hurrying to automate their first property is bad business practice.

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.  

However, it also depends what exactly those expenses are, e.g. unnecessary payroll would be something you should be able to correct (and if you lower it, you increase the value of the Facility); high flood insurance or excessive property taxes are what they are and typically cannot be reduced, very well throwing off the "industry standard".Typically we recommend buying a Facility as it is currently performing (past 12 months) and use a pro forma only for where you can realistically take it. 

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