Building an ADU is a nice way to add value but you won't get that funded by a lender. 

If something breaks, the management company fixes it. 

Instead of shelling out $60K for a $250K deal, maybe some of you can help me figure out (or give referrals) to title companies, etc, or give overall advice how to save me money from this enormous financial endeavor (closing the deal).Thanks!

I use $2500 to pay expenses and save what's left in a fund for repairs etc...So I can count on approx 5K/month in gross income. 

Screen tenants thoroughly, have a solid lease, and maintain an emergency fund for unexpected expenses.

A solution company that intrigues me is Acoustimac.

Steadily has their own product (with multiple writing companies) and then they offer policies through other carriers just as an independent agency would. 

@Greg O'Brien - Do you mind sharing your company details? 

About 5 years ago one of the sellers we bought a multi family from told us about a company that has a lot of landlords like us and we coshare insurance coverage.

I know I won’t actually be getting that right away because it should be going to savings for emergency funds for the property.