I’m open to paying the $20K to bring the mortgage current, but I want to ensure my position is protected.If the deal falls through, how can I secure my $20K so I’m not left out of pocket?

@Brady Bitter First what are you calling "securities"? 

For all multi-family properties we always handle the lawn care as there are common areas so we can't expect the tenants to care for it.When sending the security deposit claim we state the additional cost that is owed for damages even if the entire security deposit is claimed for other damages.

Quote from @James Miller: Quote from @Chris Seveney: Quote from @Stuart Udis: @Ryan Blake These investments can be secured, or at least better secured if papered correctly.

It has been my life's mission to build my own duplex, house hack it & use it to catalyze the BRRR cycle.As I get closer to breaking ground on the project, I'm still not 100% confident in it's feasibility due to the costs of land & construction considering it is mandatory to secure an appraisal 20% above build & land cost. 

Unfortunately, this reassessment is unavoidable, so you’ll need to evaluate whether transferring the property is worth the potential tax increase.If a Transfer Is Not Feasible:If the potential property tax increase makes the transfer impractical, an alternative option is for your father-in-law to secure a Home Equity Line of Credit (HELOC) on the property.

It's in high demand so we booked in 2022 to secure our dates.

If so, you can use the security deposits from both tenants to cover missed rent. 

Many traditional banks won’t touch them, and even DSCR lenders will avoid them if the build out is done prior the securing long term debt. 

Quote from @Jaren Taylor: Quote from @Chris Mason: If you have the ability to market and raise money, then you secure the down payment, and do the normal commercial mortgage process.