All of our self-storage run at basically 100% occupancy except for our most recent addition. 

Additionally, small loans like you're describing are not looked kindly upon by lenders because they're doing the same amount of work as they would on a $500k loan but for a fraction of the yield.

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.

In addition to your realtor, you'll want to reach out to local PM's, decorators or contractors, etc.

I was fine with all these numbers.Then I met with contractors...First, I wanted to add a new bathroom and approximately 450 sq ft of additional living space.

As a backup plan, if I have to go with a local PM company that only leases the entire home, could I use an addendum to add additional tenants to the existing lease while ensuring everything is legally structured?

Happy to chat if you have additional questions. 

In addition, if you're actively flipping properties in the area, I currently have time on my hands and I'd be happy to support you in one of your projects in exchange for learning in depth about the process. 

@Mark Toweya couple things - from the seller's perspective, it means the seller doesn't have to wait the full 30 years to get the proceeds, and from the buyer's perspective, hopefully in that 5 years appreciation and maybe some updates have increased the value such that when you refinance you don't have to bring any additional cash.  

There will also be closing costs to refinancing into DSCR.Lenders need 6 months to refinance a loan, anything sooner, you're probably paying a good amount of points / DSCR has to be rock solid.There also may be additional costs in maintaining your property.