Most look at a Certificate of Insurance and confirm coverage limits but best practices are to (1) become added as additional insured under contractors policy and (2) understand coverage exclusions which are not going to be detailed on an insurance certificate.

In addition to the different tracks @Chris Seveney descrubed, there is also good information on creative financing and seller financing (including what to avoid).

In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

Quote from @Victor Yang:In addition, is it possible for me and my wife to gift 36k worth of equity per year of the house (under the annual exclusion limit) and therefore have none of the costs go towards the lifetime gift limit?

In addition to offering "cash for keys" assure them that they can use you as a referral on their next tenant application, or offer them a short term-2 month lease.

Additional costs will creep in and costs seem to go up faster than rents, so I would sell and try to otherwise optimize the VA loan. 

Do not be afraid to Collateralize yourself with additional deposits to fill a vacancy. 

The only reason he did it was because it led to additional work.

If you have any additional advice please let me know!

In addition, the gas bills have shut off notices and are not being paid. (3 units are occupied and utilities are all paid by owner).