It depends on who services the 401K plan.

- own them outright- plan to owner finance at 10% down 10% interest I use a title company and attorney for closing along with servicing company once done. 

A hard money loan can lend you up to 100% of purchase and rehab money as long as that is lower than 75% of the ARV (After Repair Value) of the property.

Is it worth the risk if (a) the tenant is non-compliant and an eviction process is needed and/or (b) there could be major repairs needed. 

- Residential purchases, remodel/repairs, and re-sale (flips).

I am working with the servicer right now to confirm it can be assumed.

Since a condo would be limited in terms of physical changes, think about what services or experiences you could add like grocery shopping (assuming full kitchen), concierge, driving service, eco tours, snorkeling, etc...

Is getting $50-100/month worth the hassle of the extra tenants and repairs? 

I own and operate a high-end full service remodeling company in the Phoenix metro area.  

I know a decent amount about construction and I can offer advice or even services as a handyman.