What if we shook hands and agreed to the following (some specifics can be modified):I fund his deals out of my 401k, and he funds my deals out of HIS 401kWe offer each other identical terms and the same amount of money (say, $50K)Private, secured notes by the real estate that is being improvedWe should probably both do our due diligence on each other's deals, to make sure there is sufficient equity to get paid back on our loansTerms such as: interest only, 6%, one year balloon, to be re-paid upon sale or re-finance of the property, with option to extend/re-finance after one year (in case the unexpected happens).  

It can be worth it if you have a great deal and you have enough available to cover any unexpected expenses when they come up. 

One of the areas I learned about with RL was how to handle rentals to military personnel in cases where they are unexpectedly deployed during the lease.

This can also go the other way; if you injured someone in a car accident and the prosecutor came after you for claimable assets he/she would conduct an asset search.

The parents were an a car accident and were left to a grandmother that later past away.

It was like watching a train wreck or car accident in slow motion.

Keep the higher rate and throw that extra money in a reserve... it'll serve you far better in an unexpected vacancy or repair vs savings 22 dollars a mo.

We've increased our liability coverage - I don't trust Airbnb's "million dollar guaranty", as it specifically refuses to cover medical bills, accidents and such and only pretends to cover personal property.

That covers unexpected easements and other boundary issues.If you are unsure about the lot lines then find out what a survey would cost.

Cost of cutting and delivery to the mill is roughly 1/2 of what you will receive for the lumber.Timber property is usually listed for sale with a board foot figure included in the listing, that has been prepared by a licensed timber cruiser and which can be verified and audited.Seriously, it is one thing to buy a parcel with timber by accident, but if you want to deal in timber properties, you will be swimming with the really big sharks and you had better take the time to learn what you are doing.